Veratraldehyde → Ethyl 3-(3,4-dimethoxyphenyl)prop-2-enoate

HRID 246903Notes

Reaction equation

HRID 246903 reaction equation
[C:1]([CH:6]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:3][CH2:4][CH3:5])=[O:2].[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[CH:31]=O>ClCCl>[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[CH:31]=[CH:6][C:1]([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 8419VeratraldehydeHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

Product 1

HCID 2794876Ethyl 3-(3,4-dimethoxyphenyl)prop-2-enoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Carbethoxymethylene triphenylphosphorane (150 g, 0.3 mol) was added to a solution of 3,4-dimethoxybenzaldehyde (50 g, 0.3 mol) in dry dichloromethane (150 ml), and the mixture was stirred at room temperature overnight. The solution was concentrated to about 50 ml, and the precipitate was filtered off and washed with hexane-dichloromethane (4:1, v/v). The combined filtrates were evaporated to a residue, which was purified by silica gel chromatography using hexane-ethyl acetate (9:1, v/v) as the eluant. The title compound was isolated as a crystalline mass (65 g, 91%), m.p. 52°-53° C.

Workup

  1. concentrationThe solution was concentrated to about 50 ml
  2. filtrationthe precipitate was filtered off
  3. washwashed with hexane-dichloromethane (4:1
  4. customThe combined filtrates were evaporated to a residue, which
  5. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-77b12f613e3a4e96bf895fc158575c3d
Source dataset
uspto-grants-1987_11
Patent number
US04704462

Reaction notes

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