Water → (2E)-3-[4-(Propan-2-yl)phenyl]prop-2-en-1-ol

HRID 1017854Notes

Reaction equation

HRID 1017854 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12](OCC)=[O:13])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7](/[CH:10]=[CH:11]/[CH2:12][OH:13])=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6438317Ethyl p-isopropylcinnamateHCID 21226445Aluminium lithium hydride

Product 1

HCID 21961314(2E)-3-[4-(Propan-2-yl)phenyl]prop-2-en-1-olYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of ethyl (E)-3-(4-isopropylphenyl)-2-propenoate (20.0 g, 91.6 mmol) in tetrahydrofuran (200 ml) was added in four portions at −40° C. for 30 minutes lithium aluminum hydride (2.61 g, 68.7 mmol) and the resulting mixture was stirred at the same temperature for 30 minutes. Water was added into the reaction solution and the product was extracted twice with ethyl acetate. The combined extracts were washed with water, dried on magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel (hexane-ethyl acetate 8:1) to obtain 10.5 g (65% yield) of the oily title compound.

Workup

  1. extractionthe product was extracted twice with ethyl acetate
  2. washThe combined extracts were washed with water
  3. customdried on magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d146ac1c3fd74b0fbf4f29ae41cef248
Source dataset
uspto-grants-2002_11
Patent number
US06479536B1

Reaction notes

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