4-Hydroxybenzaldehyde → Methyl 2-(4-formylphenoxy)acetate

HRID 902769Notes

Reaction equation

HRID 902769 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:16][O:17][C:18](=[O:21])[CH2:19]Br>CN(C=O)C>[CH3:16][O:17][C:18](=[O:21])[CH2:19][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Product 1

HCID 758214Methyl 2-(4-formylphenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxybenzaldehyde (100 g, 0.818 mol) in dry DMF (1 L) was added potassium carbonate (260 g, 1.88 mol) and KI (10 g) with stirring at rt. The reaction mixture was slowly heated to 40° C. and added methylbromoacetate (104 g, 0.67 mol) with stirring and heated to 70° C. for 4 h. The reaction mixture was cooled to rt, filtered off the solid and filtrate was diluted with water (1.5 L). The aqueous mixture was extracted with EtOAc (3×750 mL), washed with 2.5% aqueous NaOH solution (2×400 mL), water and dried. The solvent was removed under vacuum to give the title compound a slight yellow solid (112 g).

Workup

  1. temperatureThe reaction mixture was slowly heated to 40° C.
  2. stirringwith stirring
  3. temperatureheated to 70° C. for 4 h
  4. temperatureThe reaction mixture was cooled to rt
  5. filtrationfiltered off the solid and filtrate
  6. additionwas diluted with water (1.5 L)
  7. extractionThe aqueous mixture was extracted with EtOAc (3×750 mL)
  8. washwashed with 2.5% aqueous NaOH solution (2×400 mL), water
  9. customdried
  10. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-7c3a2204074044cfa00889380c5166bd
Source dataset
uspto-grants-2008_04
Patent number
US07365225B2

Reaction notes

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