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

HRID 1447533

반응식

HRID 1447533 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-04b9519738864607bff2991fffc6662f
출처 데이터셋
uspto-grants-1979_12
특허 번호
US04177194

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