Hydrochloric Acid → 4-(Benzyloxy)-2-chlorobenzoic acid

HRID 1442480Notes

Reaction equation

HRID 1442480 reaction equation
C([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][C:6]=1[Cl:19])C.[OH-].[Na+].CO.Cl>O>[CH2:12]([O:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([OH:20])=[O:3])=[C:6]([Cl:19])[CH:7]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 684205954-Benzyloxy-2-chloro-benzoic acid ethyl ester

Product 1

HCID 50979854-(Benzyloxy)-2-chlorobenzoic acidYield 53.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

17.7 g (60.9 mmol) of 4-benzyloxy-2-chloro-benzoic acid ethyl ester and 4.87 g (122 mmol) of sodium hydroxide were added to a mixed solvent consisting of 180 mL of methanol and 18 mL of water followed by refluxing for 6 hours. After cooling, concentrated hydrochloric acid was added to bring to a pH of 5 followed by filtering out the precipitate. The precipitate was washed with water and dried to obtain 8.5 g of a white solid.

Workup

  1. temperatureby refluxing for 6 hours
  2. temperatureAfter cooling
  3. filtrationby filtering out the precipitate
  4. washThe precipitate was washed with water
  5. customdried

Sources & evidence

ORD record
ord-c8d03409c3244c96a95fcf0e2f0e78e4
Source dataset
uspto-grants-2010_02
Patent number
US07658979B2

Reaction notes

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