Hydrochloric Acid → 1-Phenyl-1,5-hexanedione

HRID 1084423Notes

Reaction equation

HRID 1084423 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][C:7]([OH:9])=O)(=[O:3])[CH3:2].[C:10](Cl)(=O)[C:11](Cl)=O.[Al+3].[Cl-].[Cl-].[Cl-].Cl>C1C=CC=CC=1.ClCCl.CN(C)C=O>[C:7]([CH2:6][CH2:5][CH2:4][C:1](=[O:3])[CH3:2])(=[O:9])[C:11]1[CH:10]=[CH:5][CH:4]=[CH:1][CH:2]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 184074-Acetylbutyric acidHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2385131-Phenyl-1,5-hexanedione

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

To a -10° C. solution of 4-acetylbutyric acid (1 mm, 130 mg) in benzene (1.5 cc) and dichloromethane (1.5 cc) was added oxalyl chloride (1.1 mm, 140 mg) followed by a drop of N,N-dimethylformamide; the mixture was then brought to 25° C. for 30 minutes. It was then cooled to -10° C. and AlCl3 (2 mm, 266 mg) was added portion wise and the mixture held at 0° C. for 1 hour. Ice was added, followed by 1N HCl. Then the product was extracted with ethyl acetate (2×10 cc). The organic phase was washed with dilute NaHCO3 /brine and the solvents removed in vacuo to afford the title compound.

Workup

  1. waitthe mixture held at 0° C. for 1 hour
  2. additionIce was added
  3. extractionThen the product was extracted with ethyl acetate (2×10 cc)
  4. washThe organic phase was washed with dilute NaHCO3 /brine
  5. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-09e74ff0ddb44f47a9f18ad7778ddb9e
Source dataset
uspto-grants-1991_04
Patent number
US05004743

Reaction notes

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