Hydroxyphenylacetic acid → HCID 12788538, compound

HRID 1903078Notes

Reaction equation

HRID 1903078 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH2:12](Br)[CH:13]=[CH2:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH2:14]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1)[CH:13]=[CH2:12]

Participants

6

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 12788538HCID 12788538, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

p-Hydroxyphenylacetic acid (5.0 g) is dissolved in 30 ml of dimethyl formamide, 10 ml of allyl bromide and 10 g of anhydrous potassium carbonate are added thereto, and the mixture is heated at 70°-80° C. for six hours with stirring. The reaction solution is diluted with 300 ml of water, extracted with ether, the resulting extract is dissolved in 100 ml of methanol, and the mixture is heated to reflux for one hour with 30 ml of 15% aqueous solution of potassium carbonate. The reaction solution is then concentrated in vacuo, 100 ml of water is added thereto, the mixture is washed with ether, acidified with hydrochloric acid, and extracted with ether to give 5.0 g of p-allyloxyphenylacetic acid, melting point: 61°-62° C.

Workup

  1. temperaturethe mixture is heated at 70°-80° C. for six hours
  2. extractionextracted with ether
  3. extractionthe resulting extract
  4. dissolutionis dissolved in 100 ml of methanol
  5. temperaturethe mixture is heated
  6. temperatureto reflux for one hour with 30 ml of 15% aqueous solution of potassium carbonate
  7. concentrationThe reaction solution is then concentrated in vacuo, 100 ml of water
  8. additionis added
  9. washthe mixture is washed with ether
  10. extractionextracted with ether

Sources & evidence

ORD record
ord-eb6fdea6bae64da38544845e9518fd5b
Source dataset
uspto-grants-1984_03
Patent number
US04435397

Reaction notes

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