Benzyl 4-Hydroxybenzoate → HCID 18997200, compound

HRID 374483Notes

Reaction equation

HRID 374483 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:18]([CH:20]1[O:22][CH2:21]1)Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:22]1[CH2:21][CH:20]1[CH2:18][O:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7180Benzyl 4-HydroxybenzoateHCID 11430Potassium CarbonateHCID 18430Epibromohydrin

Product 1

HCID 18997200HCID 18997200, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

In 120 ml of anhydrous N,N-dimethylformamide was dissolved 25.9 g of benzyl 4-hydroxybenzoate and 12.7 ml of epibromohydrin. To the solution was added 23.6 g of anhydrous potassium carbonate, and the mixture was stirred at 70° C. for 16 hours. The reaction mixture was concentrated under reduced pressure, and the obtained residue was extracted with ethyl acetate. The extract was washed with water, dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and purified by hexane-ethyl acetate gradient elution to give 24.5 g of the title compound as an oil (yield 76%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionthe obtained residue was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by hexane-ethyl acetate gradient elution

Sources & evidence

ORD record
ord-5e8045739872454abc255fd1fb961de3
Source dataset
uspto-grants-1996_01
Patent number
US05480899

Reaction notes

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