4-Hydroxybenzyl Alcohol → Acetic acid, [4-(hydroxymethyl)phenoxy]-, ethyl ester

HRID 2107107Notes

Reaction equation

HRID 2107107 reaction equation
[CH:1]1[C:6]([CH2:7][OH:8])=[CH:5][CH:4]=[C:3]([OH:9])[CH:2]=1.Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[OH:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:9][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:2][CH:1]=1

Participants

7

Reactant 4

HCID 1254-Hydroxybenzyl AlcoholHCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 11413157Acetic acid, [4-(hydroxymethyl)phenoxy]-, ethyl esterYield 63.8%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2.00 g of p-hydroxybenzyl alcohol, 3.23 g of ethyl bromoacetate, 2.45 g of anhydrous potassium carbonate and 15 ml of N,N-dimethylformamide was added tetra-n-butylammonium bromide in a catalytic amount. The mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with ethyl acetate and insoluble matters were filtered off. The filtrate was washed with an aqueous sodium hydroxide solution and water, in this sequence. After drying over anhydrous magnesium sulfate, the solvent was distilled off. The residue was applied to silica gel column chromatography. Elution with a solvent mixture of hexane-ethyl acetate (3:2) gave 2.16 g of oily ethyl [p-(hydroxymethyl)phenoxy]acetate.

Workup

  1. filtrationwere filtered off
  2. washThe filtrate was washed with an aqueous sodium hydroxide solution and water, in this sequence
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. washElution
  6. additionwith a solvent mixture of hexane-ethyl acetate (3:2)

Sources & evidence

ORD record
ord-4a3048df2968494ba5819b8b8a32ccd3
Source dataset
uspto-grants-1990_06
Patent number
US04933348

Reaction notes

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