Phthalaldehydic acid → 2-(2-Ethoxycarbonylpropen-1-yl)benzoic acid

HRID 733271Notes

Reaction equation

HRID 733271 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])=O.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[C:19]([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])C=CC=CC=1>CN(C)C=O>[CH2:23]([O:22][C:20]([C:19]([CH3:25])=[CH:1][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])=[O:21])[CH3:24]

Participants

4

Reactant 2

HCID 8406Phthalaldehydic acidHCID 79792Ethyl 2-(triphenylphosphoranylidene)propionate

Product 1

HCID 690545382-(2-Ethoxycarbonylpropen-1-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 5.0 g (33.3 mmol) of 2-formylbenzoic acid and 14.5 g (40.0 mmol) of ethyl 2-(triphenylphosphanylidene)propionate in 100 cm3 of dimethylformamide is stirred at a temperature in the region of 20° C. for 1 hour. After removal of the solvent, the residue is dissolved in dichloromethane and then extracted twice with sodium bicarbonate solution. The aqueous phases are combined, washed with dichloromethane and then acidified with aqueous 6N hydrochloric acid solution to a pH of between 1 and 2. After extracting twice with dichloromethane, the organic phases are combined, dried over magnesium sulfate and then concentrated. 2-(2-Ethoxycarbonylpropen-1-yl)benzoic acid is thus obtained in the form of a yellow oil, which is used directly in the following step without further purification

Workup

  1. customAfter removal of the solvent
  2. dissolutionthe residue is dissolved in dichloromethane
  3. extractionextracted twice with sodium bicarbonate solution
  4. washwashed with dichloromethane
  5. extractionAfter extracting twice with dichloromethane
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-545d938c4a0440d393ce25374513dc26
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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