Phthalaldehydic acid → t-Butyl 3-(2-carboxyphenyl)acrylate

HRID 1533260Notes

Reaction equation

HRID 1533260 reaction equation
[Cl-].[C:2]([O:6][C:7]([CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:8])([CH3:5])([CH3:4])[CH3:3].CC(C)([O-])C.[K+].[C:35]([C:38]1[CH:45]=[CH:44][CH:43]=[CH:42][C:39]=1[CH:40]=O)([OH:37])=[O:36]>O1CCCC1>[C:35]([C:38]1[CH:45]=[CH:44][CH:43]=[CH:42][C:39]=1[CH:40]=[CH:9][C:7]([O:6][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:8])([OH:37])=[O:36]

Participants

5

Reactant 3

HCID 8406Phthalaldehydic acidHCID 16211488(2-(tert-Butoxy)-2-oxoethyl)triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 53853802t-Butyl 3-(2-carboxyphenyl)acrylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (t-butoxycarbonylmethyl)-triphenylphosphonium chloride (20.7 g) in tetrahydrofuran (200 ml) was added potassium t-butoxide (5.60 g) portionwise and the mixture was stirred for 30 minutes at ambient temperature. 2-Carboxybenzaldehyde was added to the mixture. After being stirred for 1 hour the reaction mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was dissolved in 1N aqueous sodium hydroxide solution and washed with ethyl acetate. The aqueous layer was acidified by conc. hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated under reduced pressure to afford t-butyl 3-(2-carboxyphenyl)acrylate (8.3 g).

Workup

  1. stirringAfter being stirred for 1 hour the reaction mixture
  2. filtrationwas filtered
  3. customthe filtrate was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in 1N aqueous sodium hydroxide solution
  5. washwashed with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with brine
  8. customdried
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-99b38664f6b04ac9b4924ee3d4bd23bc
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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