4-Hydroxybenzyl Alcohol → HCID 54431298, compound

HRID 440578Notes

Reaction equation

HRID 440578 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].[OH:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][OH:20])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH2:12]([O:11][C:9]([CH:8]([O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][OH:20])=[CH:17][CH:16]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1)=[O:10])[CH3:13]

Participants

6

Reactant 4

HCID 1254-Hydroxybenzyl AlcoholHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 2780092Ethyl 2-(2-bromophenyl)acetate

Product 1

HCID 54431298HCID 54431298, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

41.8 g (0.172 mol) of ethyl 2-bromo-phenylacetate and 21.3 g (0.172 mol) of 4-hydroxybenzyl alcohol are dissolved in 850 ml of acetone and 24.8 g (0.18 mol) of potassium carbonate and 5.0 g (0.03 mol) of potassium iodide are added thereto. The reaction mixture is refluxed for 60 hours with stirring. Then the inorganic salts are filtered off and the residue is washed with hot acetone. The filtrate is evaporated down and the residue is purified over a silica gel column (particle size: 0.063-0.02 mm), initially using petroleum ether as eluant and then using mixtures of petroleum ether and ethyl acetate of increasing polarity (9:1, 8:2 and 7:3). The unified fractions are evaporated down in vacuo.

Workup

  1. temperatureThe reaction mixture is refluxed for 60 hours
  2. filtrationThen the inorganic salts are filtered off
  3. washthe residue is washed with hot acetone
  4. customThe filtrate is evaporated down
  5. customthe residue is purified over a silica gel column (particle size: 0.063-0.02 mm), initially using petroleum ether as eluant
  6. temperatureusing mixtures of petroleum ether and ethyl acetate of increasing polarity (9:1, 8:2 and 7:3)
  7. customThe unified fractions are evaporated down in vacuo

Sources & evidence

ORD record
ord-eefdc38978934f56b81df5f11db6d014
Source dataset
uspto-grants-1996_05
Patent number
US05519138

Reaction notes

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