Hydrochloric Acid → 3-(4-Benzyloxyphenyl)propionic acid

HRID 2227892Notes

Reaction equation

HRID 2227892 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19]C)=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl>C(O)C.C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 525519Methyl 3-[4-(benzyloxy)phenyl]propanoate

Product 1

HCID 5613723-(4-Benzyloxyphenyl)propionic acidYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of methyl 3-(4-benzyloxyphenyl)propanoate in ethanol (200 ml) and THF (100 ml) was treated with an aqueous solution of potassium hydroxide (6.7 g, 1.5 N, 101.2 mmol). The mixture was stirred at 60° C. for 1.5 hours, cooled to room temperature, adjusted to pH 3-4 with 1N HCl. The solvent was removed in vacuo to give the title material (12.8 g, 98%) as a white solid.

Workup

  1. temperaturecooled to room temperature
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4a309cbe884b4e63afea220179c6e5bf
Source dataset
uspto-grants-2002_07
Patent number
US06414179B1

Reaction notes

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