4-Hydroxybenzaldehyde → p-Formylphenyl methacrylate

HRID 2302131Notes

Reaction equation

HRID 2302131 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(#N)C.[C:13](Cl)(=[O:17])[C:14]([CH3:16])=[CH2:15]>C(N(CC)CC)C>[C:13]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)(=[O:17])[C:14]([CH3:16])=[CH2:15]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 6342AcetonitrileHCID 13528Methacryloyl chloride

Product 1

HCID 118924p-Formylphenyl methacrylate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 61 g of 4-hydroxybenzaldehyde, 400 ml of acetonitrile and 84 ml of triethylamine were added to effect the dissolution. The resulting solution was cooled to 0° C. by ice-methanol and thereto 48.4 ml of methacrylic acid chloride was gradually added dropwise. After 2 hours, the reaction solution was extracted by liquid separation with water and ethyl acetate and then subjected to silica gel column chromatography to produce the objective compound. The objective compound obtained was immediately used in the following reaction.

Workup

  1. dissolutionthe dissolution
  2. extractionthe reaction solution was extracted by liquid separation with water and ethyl acetate
  3. customto produce the objective compound
  4. customThe objective compound obtained
  5. customwas immediately used in the following reaction

Sources & evidence

ORD record
ord-8b41c1eb20ec4770ba0cebac56a5fc3b
Source dataset
uspto-grants-2002_08
Patent number
US06432615B1

Reaction notes

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