Ethanol → 4-(Benzyloxy)-2-chlorobenzoic acid

HRID 1828803Notes

Reaction equation

HRID 1828803 reaction equation
[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][C:12]([C:13]([O:15]CC2C=CC=CC=2)=[O:14])=[C:11]([Cl:25])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[OH-].[Na+]>O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][C:12]([C:13]([OH:15])=[O:14])=[C:11]([Cl:25])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 22058608Benzyl 4-benzyloxy-2-chlorobenzoate

Product 1

HCID 50979854-(Benzyloxy)-2-chlorobenzoic acidYield 97.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To benzyl 4-benzyloxy-2-chlorobenzoate (1.12 g) were added ethanol (8.8 ml), 1,4-dioxane (2.2 ml) and 1N aqueous sodium hydroxide solution (4.7 ml) and the mixture was stirred at 70° C. for 1.5 hr. The solvent was evaporated and water was added to the residue for dissolution, which was washed with diethyl ether. The aqueous layer was acidified with 1N hydrochloric acid and the precipitate was collected by filtration to give 4-benzyloxy-2-chlorobenzoic acid (810 mg) as a pale-yellow powder.

Workup

  1. customThe solvent was evaporated
  2. additionwater was added to the residue for dissolution, which
  3. washwas washed with diethyl ether
  4. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-96102719641b400bb779cc700d2a0730
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

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