Water → (Z)-8-Tetradecen-1-ol

HRID 2055074Notes

Reaction equation

HRID 2055074 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7](OC)(=[O:21])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].O.[OH-].[Na+]>C(OCC)C>[CH2:7]([OH:21])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 14309365HCID 14309365, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 6431341(Z)-8-Tetradecen-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

0.95 g lithium aluminium hydride was suspended in 150 ml diethyl ether under blanketing gas and 10 g methyl (Z)-8-tetradecenoate (4) was added dropwise at 0° C. The reaction mixture was stirred for 0.5 h at 0° C. and for 5 h at room temperature. 1 ml water and 1 ml NaOH solution (15%) were added and the mixture was filtered through silica gel. The silica gel was washed with ether, the organic phase was dried over sodium sulphate and the solvent was distilled off. (Z)-8-tetradecen-1-ol (5) was obtained.

Workup

  1. additionwas added dropwise at 0° C
  2. filtrationthe mixture was filtered through silica gel
  3. washThe silica gel was washed with ether
  4. dry with materialthe organic phase was dried over sodium sulphate
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-2151845aca98464399e4ada149434ac5
Source dataset
uspto-grants-2008_02
Patent number
US07332468B2

Reaction notes

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