4-Chlorophenol → p-Anisic acid, 4-chlorophenyl ester

HRID 1008757Notes

Reaction equation

HRID 1008757 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.[OH-].[Na+]>C(Cl)(Cl)Cl.O.ClCCl>[CH3:8][O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([O:26][C:23]2[CH:24]=[CH:25][C:20]([Cl:19])=[CH:21][CH:22]=2)=[O:15])=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 46844-ChlorophenolHCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 14798Sodium Hydroxide

Product 1

HCID 532395p-Anisic acid, 4-chlorophenyl esterYield 131.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
55 °C

Procedure

Triethylamine (6 mL) and a solution of 4.0 g of 4-methoxybenzoyl chloride (supplied from Tokyo Chemical industry) in 40 mL of chloroform were added to a solution of 6.0 g of 4-chlorophenol (supplied from Tokyo Chemical industry) in 60 mL of chloroform, and stirred at 55° C. for one hour. Then, 100 mL of dichloromethane, 200 mL of water and 25 mL of an aqueous solution of 1 N sodium hydroxide were added to the reaction solution, and the mixture was separated into two liquid phases. The organic layer was dried on sodium sulfate anhydrate and subsequently concentrated, to yield 8.1 g of the title compound.

Workup

  1. customthe mixture was separated into two liquid phases
  2. customThe organic layer was dried on sodium sulfate anhydrate
  3. concentrationsubsequently concentrated

Sources & evidence

ORD record
ord-1a670d88d90744afbb9975d1efb5b7aa
Source dataset
uspto-grants-2011_07
Patent number
US07973030B2

Reaction notes

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