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

HRID 1977271Notes

Reaction equation

HRID 1977271 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.CI.[C:19](=O)([O-])[O-].[Na+].[Na+].CN(C)[CH:27]=[O:28]>>[CH3:19][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([O:28][CH3:27])=[O:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 3015564'-Hydroxy-4-biphenylcarboxylic acid

Product 1

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

Procedure

A solution of 4-(4′-hydroxyphenyl)benzoic acid (4.98 g), methyliodide (5 ml), and sodium carbonate (7.19 g) in N,N-dimethylformamide (50 ml) was stirred for 17 hours at room temperature. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and brine. After dried over magnesium sulfate, the solution was evaporated in vacuo. The residue was triturated with n-hexane to afford methyl 4-(4′-methoxyphenyl)benzoate (5.45 g).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layer was washed with water and brine
  4. dry with materialAfter dried over magnesium sulfate
  5. customthe solution was evaporated in vacuo
  6. customThe residue was triturated with n-hexane

Sources & evidence

ORD record
ord-3cf31f5e5e3548649a2775a9acb8f3cc
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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