Ethylvanillin → HCID 12133413, compound

HRID 1906087Notes

Reaction equation

HRID 1906087 reaction equation
[CH3:1]C([O-])(C)C.[K+].O=[CH:8][C:9]1[CH:18]=[CH:17][C:15]([OH:16])=[C:11]([O:12][CH2:13][CH3:14])[CH:10]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH2:13]([O:12][C:11]1[CH:10]=[C:9]([CH:8]=[CH2:1])[CH:18]=[CH:17][C:15]=1[OH:16])[CH3:14]

Participants

5

Reactant 2

HCID 8467EthylvanillinHCID 23665647Potassium tert-butoxide

Product 1

HCID 12133413HCID 12133413, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 1140TolueneSolvent

Procedure

A suspension of methyltriphenylphosphonium bromide (1.15 mole) and potassium tert-butylate (1.33 moles) in 1 liter toluene was stirred for 1 hour at room temperature. 1.0 mole of ethylvanillin was added to the ylide thus formed. The reaction mixture was stirred for another hour and then washed with dilute hydrochloride acid. The solution was concentrated by evaporation and the residue distilled under reduced pressure. In this way 2-ethoxy-4-vinylphenol was obtained in a yield of 55%. Boiling point: 75° C./15 Pa.

Workup

  1. customthus formed
  2. stirringThe reaction mixture was stirred for another hour
  3. washwashed with dilute hydrochloride acid
  4. concentrationThe solution was concentrated by evaporation
  5. distillationthe residue distilled under reduced pressure

Sources & evidence

ORD record
ord-90550f59a9aa45ff9c63aa9d1ae6632c
Source dataset
uspto-grants-1987_03
Patent number
US04650604

Reaction notes

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