Acetone → HCID 18993862, compound

HRID 375016Notes

Reaction equation

HRID 375016 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[C:14]([O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1)(=[O:18])/[CH:15]=[CH:16]/[CH3:17].CC(C)=O>O>[C:14]([O:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([OH:3])=[O:25])=[CH:26][CH:27]=1)(=[O:18])/[CH:15]=[CH:16]/[CH3:17]

Participants

5

Reactant 3

HCID 180AcetoneHCID 11745419HCID 11745419, compoundHCID 131709961Jones' reagent

Product 1

HCID 18993862HCID 18993862, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50 ml of Jones' reagent were added dropwise while stirring within 15 minutes to a solution of 12.2 g of 4-[(E)-but-2-enoyloxy]benzaldehyde and 100 ml of acetone at 0° C. The reaction mixture was stirred at room temperature overnight, poured into water and extracted three times with 50 ml of ethyl acetate each time. The combined organic phases were extracted twice with 50 ml of 2N sodium hydroxide solution. The combined sodium hydroxide phases were acidified (pH 1) with hydrochloric acid, then extracted three times with SO ml of ethyl acetate. The organic phases were combined and washed twice with 50 ml of water, dried over magnesium sulphate, filtered and subsequently concentrated. Recrystallization of the residue from ethanol gave 10.5 g of 4-[(E)-but-2-enoyloxy]benzoic acid.

Workup

  1. extractionextracted three times with 50 ml of ethyl acetate each time
  2. extractionThe combined organic phases were extracted twice with 50 ml of 2N sodium hydroxide solution
  3. extractionextracted three times with SO ml of ethyl acetate
  4. washwashed twice with 50 ml of water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationsubsequently concentrated
  8. customRecrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-1dccc1d36955406999537e7126e48ecb
Source dataset
uspto-grants-1996_01
Patent number
US05484551

Reaction notes

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