Ethyl bromoacetate → HCID 18403741, compound

HRID 1017679Notes

Reaction equation

HRID 1017679 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[O:17][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 5613694-Benzyloxy-3-hydroxybenzaldehyde

Product 1

HCID 18403741HCID 18403741, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-benzyloxy-3-hydroxybenzaldehyde(0.5 g) in acetone (12.5 ml) was added milled potassium carbonate (1.20 g) and ethyl bromoacetate (0.48 ml), with stirring. The reaction mixture was heated under reflux for ˜1 hr, with stirring, poured into ice/water and extracted with ethyl acetate. The extracts were washed with water, saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was dissolved in dichloromethane and flash chromatographed (silica gel), eluting with dichloromethane, followed by 1% methanol:dichloromethane). The appropriate fractions were collected and combined to give 0.63 g (98%) of product, mp 36-43° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for ˜1 hr
  3. stirringwith stirring
  4. extractionextracted with ethyl acetate
  5. washThe extracts were washed with water, saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. dissolutionThe residue was dissolved in dichloromethane
  10. customflash chromatographed (silica gel)
  11. washeluting with dichloromethane
  12. customThe appropriate fractions were collected

Sources & evidence

ORD record
ord-2e12f40fd4a4498391f870f741382e96
Source dataset
uspto-grants-2002_11
Patent number
US06479495B1

Reaction notes

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