Water → 3-(3,4-Dimethoxyphenyl)prop-2-en-1-ol

HRID 246904Notes

Reaction equation

HRID 246904 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH:12]=[CH:13][C:14](OCC)=[O:15].O.[OH-].[Na+]>C(OCC)C>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH:12]=[CH:13][CH2:14][OH:15]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 2794876Ethyl 3-(3,4-dimethoxyphenyl)prop-2-enoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 3627113-(3,4-Dimethoxyphenyl)prop-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of lithium aluminum hydride (0.02 mol) in diethyl ether (20 ml) was added dropwise to a solution of ethyl 3,4-dimethoxycinnamate (9.4 g, 0.04 mol) in diethyl ether (150 ml), and the mixture was heated under reflux for 1 hour. Water (15 ml) and 2.5N sodium hydroxide (5 ml) were added to the cooled solution, and the precipitate was filtered off and washed with ether. The combined filtrates were washed with water, dried, and evaporated to dryness. The crude product was put on a column of silica gel and eluted with hexane-ethyl acetate (1.5:1, v/v). 3,4-Dimethoxycinnamyl alcohol was isolated as a crystalline mass (5.0 g, 65%), m.p. 76°-76.5° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. filtrationthe precipitate was filtered off
  4. washwashed with ether
  5. washThe combined filtrates were washed with water
  6. customdried
  7. customevaporated to dryness
  8. washeluted with hexane-ethyl acetate (1.5:1

Sources & evidence

ORD record
ord-effb652ff5df4714809fcf99180a906a
Source dataset
uspto-grants-1987_11
Patent number
US04704462

Reaction notes

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