Hydrochloric Acid → [(3-Phenylacryloyl)oxy]acetic acid

HRID 1414205Notes

Reaction equation

HRID 1414205 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][OH:3].[C:6](Cl)(=[O:15])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl>N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>[C:6]([O:3][CH2:2][C:1]([OH:5])=[O:4])(=[O:15])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 757Glycolic AcidHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 54392103[(3-Phenylacryloyl)oxy]acetic acidYield 25.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of glycolic acid (15.2 g.) in pyridine (100ml.) was added cinnamoyl chloride (33.4 g.) with stirring under cooling. The reaction mixture was stirred at room temperature for 5 hours and concentrated under reduced pressure at 50° to 60° C. The residue was adjusted to pH 1 with concentrated hydrocloric acid and extracted with ether. The extract was washed with water and a sodium chloride aqueous solution, in turn and concentrated under reduced pressure to give colorless crystals (45 g.). These crystals were dissolved in a sodium bicarbonate aqueous solution and adjusted to pH 3 to 3.5 with aqueous hydrochloric acid and extracted with ether. The extract was treated with a conventional manner to give crude product (16.5 g.). The product was recrystallized from benzene to give a product of 2-cinnamoyloxyacetic acid (10.4 g.), m.p. 116° to 121° C.

Workup

  1. temperatureunder cooling
  2. stirringThe reaction mixture was stirred at room temperature for 5 hours
  3. concentrationconcentrated under reduced pressure at 50° to 60° C
  4. extractionextracted with ether
  5. washThe extract was washed with water
  6. concentrationa sodium chloride aqueous solution, in turn and concentrated under reduced pressure
  7. customto give colorless crystals (45 g.)
  8. extractionextracted with ether
  9. additionThe extract was treated with a conventional manner
  10. customto give crude product (16.5 g.)
  11. customThe product was recrystallized from benzene

Sources & evidence

ORD record
ord-15c21423728a4348aab92e26f6da9298
Source dataset
uspto-grants-1977_01
Patent number
US04001225

Reaction notes

Loading…