Diethyl Ether → (2-acetyl-4-chlorophenoxy)-acetic Acid, 1,1-dimethylethyl Ester

HRID 38259

Reaction equation

HRID 38259 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[C:18]([O:22][C:23](=[O:26])[CH2:24]Br)([CH3:21])([CH3:20])[CH3:19].C(OCC)C>CN(C=O)C.O>[C:8]([C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[O:11][CH2:24][C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:26])(=[O:10])[CH3:9]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 740613-Chloro-6-hydroxyacetophenoneHCID 79177tert-Butyl bromoacetate

Product 1

HCID 67131695(2-acetyl-4-chlorophenoxy)-acetic Acid, 1,1-dimethylethyl Ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(5-chloro-2-hydroxyphenyl)-ethanone (2 g), potassium carbonate (1.62 g) and tert-butylbromoacetate (1.73 ml) in DMF (5 ml) was stirred at ambient temperature for 16 h. Diethyl ether and water were added and the organic layer separated, it was washed with water, aqueous potassium carbonate solution, brine, dried (Na2SO4) and the solvent removed in vacuo to give the sub-title compound (2.84 g).

Workup

  1. customthe organic layer separated
  2. washit was washed with water, aqueous potassium carbonate solution, brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-e58e506d526849c4b183a9ac5b1d2265
Source dataset
uspto-grants-2013_09
Patent number
US08524715B2

Linked notes

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