Water → Benzyl 4'-(2-hydroxyethoxy)-3',5'-dimethylbiphenyl-4-carboxylate

HRID 30756Notes

Reaction equation

HRID 30756 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][CH2:10][CH2:11][O:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([OH:28])=[O:27])=[CH:22][CH:21]=2)=[CH:15][C:14]=1[CH3:29].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[OH:9][CH2:10][CH2:11][O:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([O:28][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:27])=[CH:22][CH:21]=2)=[CH:15][C:14]=1[CH3:29]

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 230907314'-(2-Hydroxyethoxy)-3',5'-dimethylbiphenyl-4-carboxylic acid

Product 1

HCID 23090745Benzyl 4'-(2-hydroxyethoxy)-3',5'-dimethylbiphenyl-4-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl bromide (0.13 mL) was added to a mixture of 4′-(2-hydroxyethoxy}-3′,5′-dimethylbiphenyl-4-carboxylic acid (0.29 g) and potassium carbonate (0.17 g) in N,N-dimethylformamide (5 mL), and the mixture was stirred at room temperature overnight. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent:ethyl acetate/n-hexane=1/3-1/2) to afford the title compound (0.38 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent:ethyl acetate/n-hexane=1/3-1/2)

Sources & evidence

ORD record
ord-6a962746e86c44779644b6e52b1e104e
Source dataset
uspto-grants-2008_09
Patent number
US07423185B2

Reaction notes

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