Hydrochloric Acid → (2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}prop-2-enoic acid

HRID 1042608Notes

Reaction equation

HRID 1042608 reaction equation
[CH:1]1[C:6](/[CH:7]=[CH:8]/[C:9]([OH:11])=[O:10])=[CH:5][CH:4]=[C:3]([OH:12])[CH:2]=1.[OH-].[K+].Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17].Cl>O>[CH2:19]([O:18][C:16]([O:12][C:3]1[CH:4]=[CH:5][C:6](/[CH:7]=[CH:8]/[C:9]([OH:11])=[O:10])=[CH:1][CH:2]=1)=[O:17])[CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 14797Potassium HydroxideHCID 637542P-Coumaric Acid

Product 1

HCID 12876666(2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}prop-2-enoic acidYield 98.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

67 g (0.41 mol) p-cumaric acid are added to a mixture of 50.4 g (0.90 mol) potassium hydroxide and 600 ml water. 53.1 g (0.50 mol) ethyl chloroformate are added dropwise at 0° C. The reaction temperature rises to 10° C. The reaction mixture is subsequently allowed to react for 2 hours at 25° C. and acidified to pH=1 with 200 ml hydrochloric acid 7N. The product is filtered off, washed with water and dried under vacuum to give 95.3 g of (2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}acrylic acid as white powder.

Workup

  1. customrises to 10° C
  2. customto react for 2 hours at 25° C.
  3. filtrationThe product is filtered off
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-552ab2648a5e453bb5132941afb9a79c
Source dataset
uspto-grants-2013_10
Patent number
US08557922B2

Reaction notes

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