Ethyl bromoacetate → HCID 20358290, compound

HRID 2083266Notes

Reaction equation

HRID 2083266 reaction equation
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:17]([O:19][C:20](=[O:23])[CH2:21]Br)[CH3:18]>CC(C)=O>[CH2:17]([O:19][C:20]([CH2:21][O:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4])=[O:23])[CH3:18]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 20358290HCID 20358290, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 10 g of 2-hydroxyacetophenone in 40 ml of acetone, 12 g of potassium carbonate was added, and after the mixture was agitated for 1 hour at room temperature, 14 g of bromoacetic acid ethyl ester was added dropwise while stirring, and the resultant mixture was agitated for 3 hours. The reaction mixture was filtered and acetone was evaporated, leaving a residue which was extracted with ether. Evaporation of ether left a residue, which was recrystallized from petroleum ether to give 9.7 g of 2-(ethoxycarbonylmethoxy)-acetophenone, m.p. 33°-35° C.

Workup

  1. stirringwhile stirring
  2. filtrationThe reaction mixture was filtered
  3. customacetone was evaporated
  4. customleaving a residue which
  5. extractionwas extracted with ether
  6. customEvaporation of ether
  7. waitleft a residue, which
  8. customwas recrystallized from petroleum ether

Sources & evidence

ORD record
ord-ab5ca155bfcf4a9d9a43cc3048c28d25
Source dataset
uspto-grants-1978_04
Patent number
US04085135

Reaction notes

Loading…