Production Method 1

764-60-3

928-95-0

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran

Reference

Stereoselective routes to E and Z straight-chain primary allylic amines

Tomassy, Beata; Zwierzak, Andrzej, Synthetic Communications, 1998, 28(7), 1201-1214

Production Method 2

928-95-0

Reaction Conditions

1.1 Reagents: Sodium borohydride Catalysts: Methanesulfonic acid, 1,1,1-trifluoro-, erbium(3+) salt (3:1) Solvents: 2-Methyltetrahydrofuran ;  5 min, rt
1.2 Reagents: Water ;  rt

Reference

Eco-friendly stereoselective reduction of α,β-unsaturated carbonyl compounds by Er(OTf)3/NaBH4 in 2-MeTHF

Nardi, Monica; Sindona, Giovanni; Costanzo, Paola; Oliverio, Manuela; Procopio, Antonio, Tetrahedron, 2015, 71(7), 1132-1135

Production Method 3

113997-32-3

928-95-0

Reaction Conditions

1.1 Catalysts: Methanesulfonic acid, 1,1,1-trifluoro-, hafnium(4+) salt (4:1) Solvents: Methanol ;  1 h, rt
1.2 Reagents: Triethylamine ;  neutralized, rt

Reference

Hafnium Triflate as a Highly Potent Catalyst for Regio- and Chemoselective Deprotection of Silyl Ethers

Zheng, Xiu-An; Kong, Rui; Huang, Hua-Shan; Wei, Jing-Ying; Chen, Ji-Zong; et al, Synthesis, 2019, 51(4), 944-952

Production Method 4

928-95-0

Reaction Conditions

1.1 Catalysts: 12-Tungstophosphoric acid Solvents: Methanol ;  10 min, rt
1.2 Reagents: Sodium borohydride ;  30 min, rt

Reference

Direct reductive amination and selective 1,2-reduction of α,β-unsaturated aldehydes and ketones by NaBH4 using H3PW12O40 as catalyst

Heydari, Akbar; Khaksar, Samad; Akbari, Jafar; Esfandyari, Maryam; Pourayoubi, Mehrdad; et al, Tetrahedron Letters, 2007, 48(7), 1135-1138

Production Method 5

928-95-0

Reaction Conditions

1.1 Reagents: Isopropanol Catalysts: Bis(η5-cyclopentadienyl)dihydrozirconium Solvents: Isopropanol

Reference

Meerwein-Ponndorf-Verley-type reduction of dicarbonyl compounds to hydroxy carbonyl compounds and α,β-unsaturated carbonyl compounds to allylic alcohols catalyzed by zirconocene and hafnocene complexes

Nakano, Tatsuya; Umano, Shigetoshi; Kino, Yoshio; Ishii, Yasutaka; Ogawa, Masaya, Journal of Organic Chemistry, 1988, 53(16), 3752-7

Production Method 6

928-95-0

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Ethanol ;  rt

Reference

Asymmetric synthesis of chiral flavors 3-mercapto hexanol and its acetate

Ye, Honglin; Guo, Anqi; Tian, Hongyu; Sun, Baoguo; Ouyang, Tianhui, Shipin Gongye Keji, 2009, 30(12), 319-322

Production Method 7

67746-30-9

928-95-0

Reaction Conditions

1.1 Reagents: Trifluoromethanesulfonic acid Solvents: Tetrahydrofuran ,  Water
1.2 Reagents: Sodium bicarbonate Solvents: Water
1.3 Reagents: tert-Butylamine borane
1.4 Reagents: Hydrochloric acid Solvents: Water

Reference

Convenient one-pot conversion of acetals into alcohols

Lukin, Kirill A.; Yang, Cheng Xi; Bellettini, John R.; Narayanan, B. A.; Leanna, M. Robert; et al, Synlett, 1999, (1), 59-60

Production Method 8

928-95-0

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Iridium ,  Rhenium Solvents: Water ;  4 h, 0.8 MPa, 30 °C

Reference

Preparation of unsaturated alcohols by reduction of unsaturated carbonyl compounds and metal catalysts therefor

, Japan, , ,

Production Method 9

519013-65-1

928-95-0

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  rt → -78 °C
1.2 Reagents: Potassium bis(trimethylsilyl)amide Solvents: Benzene ;  10 min, -78 °C; 30 min, -78 °C; 1 h, -78 °C → rt; 30 min, rt; rt → 0 °C
1.3 Reagents: Pyridine, hydrofluoride (1:1) ;  30 min, 0 °C; 0 °C → rt; 1 h, rt

Reference

Efficient and Stereoselective Synthesis of Allylic Ethers and Alcohols

Pospisil, Jiri; Marko, Istvan E., Organic Letters, 2006, 8(26), 5983-5986

Production Method 10

27829-72-7

928-95-0

Reaction Conditions

1.1 Reagents: Diisobutylaluminum hydride Solvents: Dichloromethane ,  Hexane ;  0 °C; 1 h
1.2 Reagents: Monopotassium monosodium tartrate tetrahydrate Solvents: Water ;  2 h, rt

Reference

Regio- and diastereoselective Pd-catalyzed aminochlorocyclization of allylic carbamates: scope, derivatization, and mechanism

Papa Spadafora, Bruna; Moreira Ribeiro, Francisco Wanderson; Matsushima, Jullyane Emi; Ariga, Elaine Miho; Omari, Isaac; et al, Organic & Biomolecular Chemistry, 2021, 19(25), 5595-5606

Production Method 11

928-95-0

Reaction Conditions

1.1 Reagents: (OC-6-22)-[1,4-Diazabicyclo[2.2.2]octane-κN1,κN4]bis[tetrahydroborato(1-)-κH,κH′… Solvents: Tetrahydrofuran
1.2 Reagents: Methanol

Reference

Modified borohydride agents, (1,4-diazabicyclo[2.2.2]octane)(tetrahydroborato)zinc complex [Zn(BH4)2(dabco)]. A new ligand metal borohydride as a stable, efficient, and versatile reducing agent

Firouzabadi, Habib; Zeynizadeh, Behzad, Bulletin of the Chemical Society of Japan, 1997, 70(1), 155-167

Production Method 12

928-95-0

Reaction Conditions

1.1 Reagents: Phenylsilane Catalysts: Cobalt, [2,6-bis[1-[[3-(diphenylphosphino-κP)propyl]imino-κN]ethyl]phenyl-κC]-, … ;  2 min, 25 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  2 h, 25 °C

Reference

An aryl diimine cobalt(I) catalyst for carbonyl hydrosilylation

Sharma, Anuja; So, Sangho; Kim, Jun-Hyeong; MacMillan, Samantha N.; Baik, Mu-Hyun; et al, Chemical Communications (Cambridge, 2022, 58(77), 10793-10796

Production Method 13

105-36-2

928-95-0

Reaction Conditions

1.1 Reagents: Sodium bicarbonate ,  Triphenylphosphine Solvents: Water ;  12 h, rt
1.2 Reagents: Diisobutylaluminum hydride Solvents: Dichloromethane ;  2 h, -78 °C

Reference

Copper-Catalyzed Azide-Ynamide Cyclization to Generate α-Imino Copper Carbenes: Divergent and Enantioselective Access to Polycyclic N-Heterocycles

Liu, Xin; Wang, Ze-Shu; Zhai, Tong-Yi; Luo, Chen; Zhang, Yi-Ping; et al, Angewandte Chemie, 2020, 59(41), 17984-17990

Production Method 14

764-60-3

928-95-0

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  rt → 5 °C
1.2 Reagents: Vitride Solvents: Toluene ;  0 - 20 °C; 5 h, 20 °C → 25 °C; 25 °C → 10 °C
1.3 Reagents: Water ;  0 - 15 °C

Reference

Process for preparation of α-amino-β-hydroxycarbonyl compounds

, World Intellectual Property Organization, , ,

Production Method 15

928-95-0

Reaction Conditions

1.1 Catalysts: Zinc 2-ethylhexanoate ,  Sodium borohydride Solvents: Diisopropyl ether
1.2 Reagents: Poly(methylhydrosiloxane)
1.3 Reagents: Sodium hydroxide Solvents: Water

Reference

Selective Reduction of Carbonyl Compounds by Polymethylhydrosiloxane in the Presence of Metal Hydride Catalysts

Mimoun, Hubert, Journal of Organic Chemistry, 1999, 64(7), 2582-2589

Production Method 16

928-95-0

Reaction Conditions

1.1 Reagents: Isopropanol Catalysts: Zirconium hydroxide (Zr(OH)2)

Reference

The catalytic reduction of aldehydes and ketones with 2-propanol over hydrous zirconium oxide

Shibagaki, Makoto; Takahashi, Kyoko; Matsushita, Hajime, Bulletin of the Chemical Society of Japan, 1988, 61(9), 3283-8

Production Method 17

928-95-0

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Ethanol ;  rt; 1.5 h, rt

Reference

Preparation of optically active flavors 3-(methylthio)hexanol and its acetate

Yu, Jiefei; Tian, Hongyu; Sun, Baoguo; Ouyang, Tianhui, Jingxi Huagong, 2010, 27(4), 369-373

Production Method 18

27829-72-7

928-95-0

Reaction Conditions

1.1 Reagents: Diisobutylaluminum hydride Solvents: Dichloromethane ,  Toluene ;  -78 °C; -78 °C → rt; overnight, rt
1.2 Reagents: Methanol ;  rt

Reference

First synthesis of 3-S-glutathionylhexanal-d8 and its bisulfite adduct

Muhl, Jennifer R. ; Pilkington, Lisa I.; Deed, Rebecca C., Tetrahedron Letters, 2020, 61(28),

Production Method 19

928-95-0

Reaction Conditions

1.1 Reagents: Sodium hydroxide Catalysts: Tetrabutylammonium bromide Solvents: Water ;  < 20 °C; 3 h, 55 °C

Reference

Preparation of trans-2-hexenol and trans-2-hexenoic acid

, China, , ,

Production Method 20

930-22-3

928-95-0

Reaction Conditions

1.1 Solvents: Benzene ,  Water

Reference

New four-carbon-atom homologation involving the free-radical chain reaction of 1,3-butadiene monoxide with organoboranes. Synthesis of 4-alkyl-2-buten-1-ols from olefins via hydroboration

Brown, Herbert Charles; Suzuki, Akira; Miyaura, Norio; Itoh, Mitsuomi; Holland, George W.; et al, Journal of the American Chemical Society, 1971, 93(11), 2792-3

(E)-Hex-2-en-1-ol Raw materials

• (2E)-2-Hexenoic Acid Ethyl Ester
• trans-2-Hexenal diethyl acetal
• Silane, (1,1-dimethylethyl)[(2E)-2-hexenyloxy]dimethyl-
• Butadiene monoxide
• Ethyl bromoacetate
• 2-Hexyn-1-ol
• 1H-Tetrazole,5-[[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]sulfonyl]-1-phenyl-

(E)-Hex-2-en-1-ol Preparation Products

• (E)-Hex-2-en-1-ol (928-95-0)

• 1. Achieving crystal-induced room temperature phosphorescence and reversible photochromic properties by strong intermolecular interactions?
  Fuming Xiao,Mengzhu Wang,Yunxiang Lei,Wenbo Dai,Yunbing Zhou,Miaochang Liu,Wenxia Gao,Xiaobo Huang,Huayue Wu J. Mater. Chem. C, 2020,8, 17410-17416
• 2. An AuNPs-functionalized AlGaN/GaN high electron mobility transistor sensor for ultrasensitive detection of TNT?
  Ying Li,Weirong Yao,Yunfei Xie,Renjun Pei RSC Adv., 2015,5, 98724-98729
• 3. Agricultural
  Analyst, 1936,61, 569-570
• 4. An all-solid-state asymmetric device based on a polyaniline hydrogel for a high energy flexible supercapacitor?
  Hamid Heydari,Mohammad B. Gholivand New J. Chem., 2017,41, 237-244
• 5. An apparatus for determining small amounts of alchohol in sour milk and urine
  Analyst, 1964,89, 272-275

• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Fatty Acyls Fatty alcohols

• 97259-62-6(2,6-Octadien-1-ol,(E,Z)- (9CI))
• 106310-19-4(Benzene, 4-isocyanato-2-methyl-1-[4-[(trifluoromethyl)thio]phenoxy]-)
• 84117-75-9(2,6-Octadiene-1,8-diol, (Z,Z)-)
• 7786-44-9(2,6-Nonadien-1-ol)
• 928-94-9(cis-2-Hexen-1-ol)
• 5820-89-3(2,6-Nonadien-1-ol,(E,E)- (8CI,9CI))
• 28069-72-9(trans,cis-2,6-Nonadien-1-ol)
• 2305-21-7(2-Hexen-1-ol)
• 62019-06-1(2,6-Heptadien-1-ol, (2E)-)
• 24532-11-4(2,6-Octadien-1-ol)