Ethyl bromoacetate → HCID 54158312, compound

HRID 1016741Notes

Reaction equation

HRID 1016741 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].C(=O)([O-])[O-].[K+].[K+].[OH:14][C:15]1[CH:22]=[C:21]([CH3:23])[C:20]([CH3:24])=[CH:19][C:16]=1[CH:17]=[O:18]>CC(C)=O>[CH:17]([C:16]1[CH:19]=[C:20]([CH3:24])[C:21]([CH3:23])=[CH:22][C:15]=1[O:14][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:18]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 71720572-hydroxy-4,5-dimethylbenzaldehyde

Product 1

HCID 54158312HCID 54158312, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.808 ml of ethyl bromoacetate and 1 g of potassium carbonate were added to a solution of 838 mg of 2-hydroxy-4,5-dimethylbenzaldehyde (J.Chem.Soc. (1953) 820) in 150 ml of acetone. The suspension obtained was heated to reflux overnight and then filtered. The filtrate was concentrated. The crude product was isolated by extraction and purified by chromatography on silica gel and yielded 952 mg of ethyl (2-formyl-4,5-dimethyl-phenoxy)-acetate as a pale yellow solid.

Workup

  1. customThe suspension obtained
  2. temperaturewas heated
  3. temperatureto reflux overnight
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customThe crude product was isolated by extraction
  7. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-112fa884fb684a30959df33e358c058a
Source dataset
uspto-grants-2002_11
Patent number
US06476264B2

Reaction notes

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