Water → HCID 53892090, compound

HRID 275868Notes

Reaction equation

HRID 275868 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9](=[O:12])([O-])[O-:10].[K+].[K+].[OH2:15]>CN(C)C=O>[CH2:1]([O:10][C:9](=[O:12])[C:5]1[CH:6]=[CH:7][C:2]([C:1]2[CH:6]=[CH:7][C:2]([O:15][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:3][CH:4]=2)=[CH:3][CH:4]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 53892090HCID 53892090, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-(41-Hydroxyphenyl)benzoic acid (2.0 g) was dissolved in N,N-dimethylformamide (30 ml). To the solution were added benzyl bromide (3.99 g) and potassium carbonate (3.86 g). The mixture was stirred for 3 hours at 80° C. The reactiontmixture was poured into water (100 ml), which was subjected to extraction with ethyl acetate (150 ml). The organic layer was washed with 5% potassium hydrogensulfate, which was then washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off to leave 4-(4′-benzyloxyphenyl)-benzoic acid benzyl ester as a scale-like crystalline product (3.4 g). m.p.: 138-140° C.

Workup

  1. extractionwas subjected to extraction with ethyl acetate (150 ml)
  2. washThe organic layer was washed with 5% potassium hydrogensulfate, which
  3. washwas then washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-ce1aafaf53a841b99baf5b6660cf85dc
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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