3-Hydroxybenzaldehyde → Ethyl 2-(3-formylphenoxy)acetate

HRID 1597857Notes

Reaction equation

HRID 1597857 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:15]([O:14][C:12]([CH2:11][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])=[O:13])[CH3:16]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 7748Ethyl bromoacetate2×HCID 11430Potassium Carbonate

Product 1

HCID 1494377Ethyl 2-(3-formylphenoxy)acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 3-hydroxybenzaldehyde (5.17 g, 42.34 mmol), K2 CO3 (5.85 g) and acetone (50 ml) was added ethyl bromoacetate (5.2 ml). The reaction mixture was stirred at room temperature overnight, additional K2CO3 (1 equivalent) was added, the mixture was stirred for one hour, then additional ethyl bromoacetate (0.5 equivalents) was added and the mixture was stirred at room temperature until the reaction was complete. The reaction mixture was filtered, water was added to the filtrate and the solvent was removed. The residue was dissolved in ether, extracted with 1M NaOH (2×100 ml), and the ether layer was dried over MgSO4 and stripped to afford, as a liquid, 7.89 g of 3-(ethoxycarbonylmethoxy) benzaldehyde.

Workup

  1. stirringthe mixture was stirred for one hour
  2. stirringthe mixture was stirred at room temperature until the reaction
  3. filtrationThe reaction mixture was filtered
  4. additionwater was added to the filtrate
  5. customthe solvent was removed
  6. dissolutionThe residue was dissolved in ether
  7. extractionextracted with 1M NaOH (2×100 ml)
  8. dry with materialthe ether layer was dried over MgSO4

Sources & evidence

ORD record
ord-dab5f8db7da242c284b1cb35a470c754
Source dataset
uspto-grants-1998_04
Patent number
US05736548

Reaction notes

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