Potassium Carbonate → 3-(Cyclopropylmethoxy)-4-methoxybenzaldehyde

HRID 2394495Notes

Reaction equation

HRID 2394495 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].Cl[CH2:13][CH:14]1[CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:14]1([CH2:13][O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=2[O:10][CH3:11])[CH:5]=[O:6])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12127IsovanillinHCID 80013(Chloromethyl)cyclopropane

Product 1

HCID 222466233-(Cyclopropylmethoxy)-4-methoxybenzaldehydeYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A vigorously stirred mixture of 3-hydroxy-4-methoxybenzaldehyde (20 g, 131 mmol), chloromethylcyclopropane (18.2 mL, 197 mmol) and powdered potassium carbonate (27.3 g, 197 mol) in dimethylformamide (400 mL) was heated under an argon atmosphere at 80° C. for 9 h. The mixture was allowed to cool and was filtered through Celite. The filtrate was concentrated under reduced pressure, the residue was extracted twice with ethyl acetate, the organic extract was washed five times with saturated aqueous sodium carbonate and was dried (sodium sulfate). The solvent was removed in vacuo to provide an off-white solid (21.2 g, 78%): m.p. 67°-69° C.

Workup

  1. temperatureto cool
  2. filtrationwas filtered through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. extractionthe residue was extracted twice with ethyl acetate
  5. extractionthe organic extract
  6. washwas washed five times with saturated aqueous sodium carbonate
  7. dry with materialwas dried (sodium sulfate)
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0e52c5222d4e4236ba07e834d8466c53
Source dataset
uspto-grants-1998_09
Patent number
US05811455

Reaction notes

Loading…