Ethylvanillin → methyl 3(E)-(3-ethoxy-4-hydroxyphenyl)acrylate

HRID 987876Notes

Reaction equation

HRID 987876 reaction equation
C1(P(=C=[CH:21][C:22]([O:24][CH3:25])=[O:23])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:26]([O:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][C:36]=1[OH:37])[CH:32]=O)[CH3:27]>C1(C)C=CC=CC=1>[CH2:26]([O:28][C:29]1[CH:30]=[C:31](/[CH:32]=[CH:21]/[C:22]([O:24][CH3:25])=[O:23])[CH:34]=[CH:35][C:36]=1[OH:37])[CH3:27]

Participants

4

Reactant 2

HCID 8467EthylvanillinHCID 12530579HCID 12530579, compound

Product 1

HCID 12641148methyl 3(E)-(3-ethoxy-4-hydroxyphenyl)acrylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.1 g (6.32 mmol) of methyl (triphenylphosphoranylidene)acrylate are added, at room temperature, to a solution of 1.0 g (6.01 mmol) of 3-ethoxy-4-hydroxybenzaldehyde and 10 ml of toluene. The reaction is then allowed to continue for 1 hour at room temperature, the reaction suspension is clarified by filtration over a silica gel bed and the filtrate is evaporated down. Chromatography of the residue over silica gel using toluene/ethyl acetate gives methyl 3(E)-(3-ethoxy-4-hydroxyphenyl)acrylate.

Workup

  1. filtrationthe reaction suspension is clarified by filtration over a silica gel bed
  2. customthe filtrate is evaporated down

Sources & evidence

ORD record
ord-1a44a90248614d7181993b25fc60881f
Source dataset
uspto-grants-2003_10
Patent number
US06632909B2

Reaction notes

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