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

HRID 1792956Notes

Reaction equation

HRID 1792956 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-6b8a37e00587416cad369e3624f6633b
Source dataset
uspto-grants-2006_07
Patent number
US07078428B2

Reaction notes

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