Hydrochloric Acid → Ethyl 2-(4-hydroxyphenoxy)acetate

HRID 565117Notes

Reaction equation

HRID 565117 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].Br[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].[OH-].[Na+].Cl>CN(C=O)C.O>[OH:2][C:1]1[CH:8]=[CH:7][C:5]([O:6][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 785HydroquinoneHCID 7748Ethyl bromoacetateHCID 14798Sodium Hydroxide

Product 1

HCID 13187337Ethyl 2-(4-hydroxyphenoxy)acetateYield 13,437.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of hydroquinone (24 g, 0.22 mmol) and ethyl bromoacetate (24 mL, 0.22 mol) in DMF (300 mL) was added 10M aq. NaOH(22 mL, 0.22 mol). The mixture was stirred at 0° C. for 1 h, diluted with H2O, acidified with 6M aq. HCl and extracted with EtOAc. The EtOAc extract was dried (anhydrous MgSO4) and concentrated in vacuo. The residue was swished with Et2O to give ethyl 4-hydroxyphenoxy-acetate (5.8 g) as a white powder.

Workup

  1. extractionextracted with EtOAc
  2. extractionThe EtOAc extract
  3. dry with materialwas dried (anhydrous MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a161c3552d724cdaa937bad98518fc4d
Source dataset
uspto-grants-2001_01
Patent number
US06169188A

Reaction notes

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