Water → 3,7-Dimethyl-4-hydroxy-6-octen-1-ol

HRID 1447533

Reaction equation

HRID 1447533 reaction equation
[CH3:1][CH:2]([C:8](=[O:14])[CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])[CH2:3][C:4](OC)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)(O)[O-].[Na+].O>CCOCC.C(OCC)(=O)C>[CH3:1][CH:2]([CH:8]([OH:14])[CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])[CH2:3][CH2:4][OH:5]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 15340230Methyl 3,7-dimethyl-4-oxo-6-octenoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 136688813,7-Dimethyl-4-hydroxy-6-octen-1-olYield 863.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 3,7-dimethyl-4-oxo-6-octenoate (68 g, 34 mmole) in ether (10 ml) is added to a mixture of lithium aluminum hydride (1.3 g, 34 mmole) and ether (150 ml) at 0°. After the addition is complete the mixture is allowed to warm to room temperature and stirred for 1 hour, after which it is cooled to 0° and carefully added to a 5% aqueous sodium bicarbonate solution (50 ml). The resulting mixture is treated with water (100 ml) and ethyl acetate (300 ml). The organic phase is separated, dried (Na2SO4) and the solvent is removed in vacuo to give a colorless oil (50.6 g, 94%). This material shows one spot on TLC (silica gel 50% ethyl acetate in hexane) and is not further purified.

Workup

  1. additionAfter the addition
  2. temperatureafter which it is cooled to 0°
  3. customThe organic phase is separated
  4. dry with materialdried (Na2SO4)
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-04b9519738864607bff2991fffc6662f
Source dataset
uspto-grants-1979_12
Patent number
US04177194

Linked notes

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