Hexanal → 1-Nonen-4-ol

HRID 2245746Notes

Reaction equation

HRID 2245746 reaction equation
[CH:1](=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:8](Cl)[CH:9]=[CH2:10].O.O.[Sn](Cl)Cl>[Cu].O>[OH:7][CH:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:10][CH:9]=[CH2:8]

Participants

6

Reactant 3

HCID 6184HexanalHCID 7850Allyl chlorideHCID 61436Stannous chloride dihydrate

Product 1

HCID 1419751-Nonen-4-ol

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

3500 ml water, 200 g hexanal (2 mol) and 305 g allyl chloride (4 mol), 900 g tin(II) chloride dihydrate (2 mol) and 25 g copper powder (0.4 mol) was added into a 61 flask. The reaction mixture was stirred at ca. 30° C. for 8 h. The organic phase was separated by decantation or centrifugation and the crude raw product distilled in vacuo to give 4-hydroxy-1-nonene. MS: m/z 141 (M-1), 101 (M-C3H5), 124 (M-18), 83 (101-18), 55 (83-C2H4).

Workup

  1. customThe organic phase was separated by decantation or centrifugation
  2. distillationthe crude raw product distilled in vacuo

Sources & evidence

ORD record
ord-531e5312285443be89e9db694cac0df4
Source dataset
uspto-grants-2010_03
Patent number
US07683187B2

Reaction notes

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