Dichloromethane → Acetoacetic Acid

HRID 1834488Notes

Reaction equation

HRID 1834488 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([CH3:3])=[CH2:2].C(Cl)Cl.C([O:17][C:18](=[O:20])[CH3:19])(=O)C>[OH-].[Na+]>[CH3:6][C:7]([CH2:19][C:18]([OH:17])=[O:20])=[O:10].[C:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([CH3:3])=[CH2:2]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 584247p-Isopropenylphenol

Product 2

HCID 96Acetoacetic AcidHCID 584247p-Isopropenylphenol

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
10 °C

Procedure

240 g (0.9 mol) of dimeric p-isopropenyl phenol are dissolved under nitrogen in 800 g of 10% by weight aqueous sodium hydroxide. 400 ml of methylene chloride are then added and the reaction mixture is cooled to 10° C. 375 g (3.6 mols) of acetic acid anhydride are added dropwise with stirring at that temperature, and the mixture subsequently stirred for another hour at 5° to 10° C. The aqueous phase is then separated off, the organic phase is washed with water, bicarbonate solution and again with water and then dried over calcined sodium sulphate. Removal of the solvent by distillation is followed by distillation in a high vacuum, giving 285 g (90% of the theoretical) of diacetate of dimeric p-isopropenyl phenol.

Workup

  1. stirringthe mixture subsequently stirred for another hour at 5° to 10° C
  2. customThe aqueous phase is then separated off
  3. washthe organic phase is washed with water, bicarbonate solution and again with water
  4. customdried
  5. customRemoval of the solvent
  6. distillationby distillation
  7. distillationis followed by distillation in a high vacuum

Sources & evidence

ORD record
ord-1589125b6ca54662b300ca70b64aed91
Source dataset
uspto-grants-1978_01
Patent number
US04070392

Reaction notes

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