p-Anisoyl chloride → HCID 808296, compound

HRID 1008752Notes

Reaction equation

HRID 1008752 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.[F: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]([F:19])=[CH:21][CH:22]=2)=[O:15])=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 97324-FluorophenolHCID 14798Sodium Hydroxide

Product 1

HCID 808296HCID 808296, compoundYield 140.3%

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-fluorophenol (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-1855be5c86214de1a53c77eff014cbf8
Source dataset
uspto-grants-2011_07
Patent number
US07973030B2

Reaction notes

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