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

HRID 1072893Notes

Reaction equation

HRID 1072893 reaction equation
C(O)C.[OH-].[Na+].[CH2:6]([O:13][C:14]1[CH:29]=[CH:28][C:17]([C:18]([O:20]CC2C=CC=CC=2)=[O:19])=[C:16]([Cl:30])[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>O1CCOCC1>[CH2:6]([O:13][C:14]1[CH:29]=[CH:28][C:17]([C:18]([OH:20])=[O:19])=[C:16]([Cl:30])[CH:15]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=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

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

Workup

  1. customThe solvent was evaporated
  2. additionwater was added to the residue
  3. dissolutionto dissolve the same
  4. washAfter washing with ether
  5. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-84cd3ddcc9de4fc1bf58f5a50d0bd487
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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