Water → (E)-methyl 2-(2-formylphenyl)-3-methoxypropenoate

HRID 1493492Notes

Reaction equation

HRID 1493492 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[CH:14]\[O:15][CH3:16])/[C:10]([O:12][CH3:13])=[O:11].P([O-])([O-])(O)=[O:18].[Na+].[Na+].P([O-])([O-])(O)=O.[K+].[K+].O>CS(C)=O>[CH:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[CH:14]\[O:15][CH3:16])/[C:10]([O:12][CH3:13])=[O:11])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 24203Sodium Phosphate, DibasicHCID 24450Potassium Phosphate, DibasicHCID 9925856(E)-methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylate

Product 1

HCID 22872991(E)-methyl 2-(2-formylphenyl)-3-methoxypropenoateYield 40%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (E)-methyl 2-[2-(bromomethyl)phenyl]-3-methoxypropenoate (10.0 g, 90% pure), sodium hydrogen orthophosphate dibasic (Na2HPO4, 5.74 g) and potassium hydrogen monophosphate monobasic (KH2PO4.0.55 g) in DMSO (20 ml) was heated at 80° C. for 1 hour and then at 110° C. for a further hour (compare J H Babler, M J Coghlan, M Feng and P Fries, J.Org.Chem., 1979, 44, 1716). After cooling, the reaction mixture was poured into water and extracted with ether. The extracts were washed with brine, dried, concentrated and chromatographed using ether as eluant to give (E)-methyl 2-(2-formylphenyl)-3-methoxypropenoate (2.77 g, 40% yield) as a white crystalline solid, m.p. 67°-69° C.

Workup

  1. waitat 110° C. for a further hour (compare J H Babler, M J Coghlan, M Feng and P Fries, J.Org.Chem., 1979, 44, 1716)
  2. temperatureAfter cooling
  3. extractionextracted with ether
  4. washThe extracts were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customchromatographed

Sources & evidence

ORD record
ord-5b85cd92c27f4e75af5eb52a97018919
Source dataset
uspto-grants-1991_06
Patent number
US05021581

Reaction notes

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