Carbon Dioxide → Benzoylacetic acid

HRID 1283853Notes

Reaction equation

HRID 1283853 reaction equation
C(C1(C([O-])=O)C(O)=C(C(C)(C)C)C=C(C)C1)(C)(C)C.[K+].[C:21](=[O:23])=[O:22].[C:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])[CH3:25]>C1(C)C=CC=CC=1>[C:24]([CH2:25][C:21]([OH:23])=[O:22])(=[O:26])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 7410AcetophenoneHCID 68144010HCID 68144010, compound

Product 1

HCID 97045Benzoylacetic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

6.7 g of potassium 2,6-di-t-butyl-p-cresolate in 30 cc of toluene were introduced into a 4-neck flask, having a capacity of 100 cc, provided with stirrer, thermometer and gas inlet pipe. In a carbon dioxide atmosphere 3.1 g of acetophenone (phenate: substrate molar ratio = 1 : 1) were added; the whole was stirred at 20°C for 4 hours and then acidified with cold sulphuric acid at 10% concentration. The organic phase separated, and was then extracted with a 10% sodium carbonate aqueous solution. 0.9 g of benzoylacetic acid were isolated by acidification and extraction with ether. 2.3 g of acetophenone were recovered from the organic phase.

Workup

  1. customprovided with stirrer
  2. concentrationacidified with cold sulphuric acid at 10% concentration
  3. customThe organic phase separated
  4. extractionwas then extracted with a 10% sodium carbonate aqueous solution

Sources & evidence

ORD record
ord-5c32a81745d04192952fc09df2ada626
Source dataset
uspto-grants-1976_08
Patent number
US03976677

Reaction notes

Loading…