Hydrochloric Acid → (2Z)-5-(4-Chlorophenyl)-3-phenylpent-2-enoic acid

HRID 1402874Notes

Reaction equation

HRID 1402874 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]/[C:10](/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11]/[C:12]([O:14]CC)=[O:13])=[CH:4][CH:3]=1.[OH-].[Na+].O.Cl>CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9]/[C:10](/[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:11]/[C:12]([OH:14])=[O:13])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 53486130HCID 53486130, compound

Product 1

HCID 44141940(2Z)-5-(4-Chlorophenyl)-3-phenylpent-2-enoic acidYield 73.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (Z)-ethyl 5-(4-chlorophenyl)-3-phenylpent-2-enoate (139 mg) and 4M NaOH (1.1 ml) in EtOH (10 ml) was stirred at rt for 4 h. The mixture was poured into water (30 ml), acidified to pH 2 with 10% HCl and extracted with ethyl acetate (3×20 ml). The combined organic layers were washed with brine (20 ml), dried (MgSO4) and evaporated to afford a crude, which was purified by crystallisation from hexane/ethylacetate to afford (Z)-5-(4-chlorophenyl)-3-phenylpent-2-enoic acid (93 mg) as colourless solid.

Workup

  1. extractionextracted with ethyl acetate (3×20 ml)
  2. washThe combined organic layers were washed with brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto afford a crude, which
  6. customwas purified by crystallisation from hexane/ethylacetate

Sources & evidence

ORD record
ord-38346cd9830f4d169d6e4fa8ab434aaf
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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