Dimethylformamide → Methyl 4'-methoxy(1,1'-biphenyl)-4-carboxylate

HRID 1072702

Reaction equation

HRID 1072702 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.IC.CN(C)[CH:21]=[O:22].[C:24](OCC)(=O)C>O>[CH3:24][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([O:22][CH3:21])=[O:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 3015564'-Hydroxy-4-biphenylcarboxylic acid

Product 1

HCID 1393415Methyl 4'-methoxy(1,1'-biphenyl)-4-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixed solution of 4-(4′-hydroxyphenyl)benzoic acid (10.0 g, 4.67 mmol), iodomethane (19.9 g, 14.0 mmol) and N,N-dimethylformamide (80 ml) was stirred at 60° C. for 3 hours. To the obtained mixture was added ethyl acetate (200 ml) and water (150 ml), the mixture was stirred and the organic layer was separated. The organic layer was washed with 5% aqueous potassium hydrogen sulfate and water, and dried over sodium sulfate anhydride. The solvent was concentrated under reduced pressure and the object compound (10.5 g) was obtained from the residue as colorless crystals. Melting point: 177-178° C.

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with 5% aqueous potassium hydrogen sulfate and water
  3. dry with materialdried over sodium sulfate anhydride
  4. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0eed00481a0b48a6bccb4ed8e2a762dd
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Linked notes

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