Water → HCID 11974709, compound

HRID 1393862Notes

Reaction equation

HRID 1393862 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1.O>CC(C)=O>[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=2)=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 96024-Fluorobenzyl chlorideHCID 11430Potassium CarbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 11974709HCID 11974709, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 4-hydroxyphenylacetate (6.00 g, 36.11 mmol) was dissolved in acetone (72 ml), and potassium carbonate (7.49 g, 54.16 mmol) and 4-fluorobenzyl chloride (6.47 ml, 54.16 mmol) were added thereto. After being refluxed for 24 hours, the mixture, with water added thereto, was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over MgSO4, and then the solvent was evaporated out. The obtained residue was purified by silica gel column chromatography (5% ethyl acetate/hexane), to give methyl 2-{4-[(4-fluorobenzyl)oxy]phenyl}acetate (9.18 g, 93%).

Workup

  1. temperatureAfter being refluxed for 24 hours
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over MgSO4
  5. customthe solvent was evaporated out
  6. customThe obtained residue was purified by silica gel column chromatography (5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e66d847f2ea0456ebe2346337f1e510b
Source dataset
uspto-grants-2008_03
Patent number
US07348017B2

Reaction notes

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