3',4'-Dimethoxycinnamic acid → 3-(3,4-Dimethoxyphenyl)prop-2-en-1-ol

HRID 246905

Reaction equation

HRID 246905 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH:12]=[CH:13][C:14](O)=[O:15]>C1COCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH:12]=[CH:13][CH2:14][OH:15]

Participants

4

Reactant 2

HCID 168483',4'-Dimethoxycinnamic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 3627113-(3,4-Dimethoxyphenyl)prop-2-en-1-olYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium aluminum hydride (0.1 mol) in THF (100 ml) was added dropwise to a stirred suspension of 3,4-dimethoxycinnamic acid (41.6 g, 0.2 mol) in THF (150 ml) at room temperature. After the addition, the mixture was stirred for 2 hous, and the solution was evaporated in vacuo to a residue, which was partitioned between dichloromethane and aqueous sodium hydroxide. The organic layer was washed three times with water, dried, and evaporated to an oil. Crystallization from ethyl acetate-hexane gave 3,4-dimethoxycinnamyl alcohol (24 g, 62%), m.p. 76°-77° C.

Workup

  1. additionAfter the addition
  2. customthe solution was evaporated in vacuo to a residue, which
  3. customwas partitioned between dichloromethane and aqueous sodium hydroxide
  4. washThe organic layer was washed three times with water
  5. customdried
  6. customevaporated to an oil
  7. customCrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-79c50db94cbb420785acc3daae30fdb5
Source dataset
uspto-grants-1987_11
Patent number
US04704462

Linked notes

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