Hydrochloric Acid → HCID 10551523, compound

HRID 322854Notes

Reaction equation

HRID 322854 reaction equation
[CH2:1](/[C:8](=[CH:14]\[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:17][C:16]=1[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)/[C:9]([O:11]CC)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO.O.[OH-].[K+]>[CH2:1](/[C:8](=[CH:14]\[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:17][C:16]=1[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)/[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 10767021HCID 10767021, compound

Product 1

HCID 10551523HCID 10551523, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14797Potassium HydroxideSolvent2×

Procedure

A mixture of ethyl (E)-2-benzyl-3-(2,4-dibenzyloxyphenyl)acrylate (1.5 g) and aqueous potassium hydroxide in methanol (50 mL, 15%) is stirred and heated at reflux for 3 hours. The reaction mixture is diluted with water (30 mL) plus 3 N potassium hydroxide solution (5 mL), acidified to pH 1 by addition of concentrated hydrochloric acid and the resulting solid filtered. Recrystallisation from a mixture of ethyl acetate and pentane gives E-2-benzyl-3-(2,4-dibenzyloxyphenyl)acrylic acid (1.13 g) as a white solid, m.p. 175-176° C. [Elemental analysis:- C,79.7; H,5.72%. Calculated:- C,80.0; H,5.82%].

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. filtrationthe resulting solid filtered
  4. customRecrystallisation
  5. additionfrom a mixture of ethyl acetate and pentane

Sources & evidence

ORD record
ord-a896a5f2193f44978f13a3e2aa4c3ac4
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

Loading…