Hydrochloric Acid → Methyl 4-(2-oxopropyl)benzoate

HRID 1906953Notes

Reaction equation

HRID 1906953 reaction equation
S(S([O-])=O)([O-])(=O)=[O:2].[Na+].[Na+].[C:10]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21](=NO)[CH3:22])=[CH:16][CH:15]=1)([O:12][CH3:13])=[O:11].Cl>O.CO>[C:10]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21](=[O:2])[CH3:22])=[CH:16][CH:15]=1)([O:12][CH3:13])=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 656671Sodium PyrosulfiteHCID 867397271-(4-Carbomethoxyphenyl)propan-2-one oxime

Product 1

HCID 11137970Methyl 4-(2-oxopropyl)benzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium metabisulphite (131 g) in water (300 ml) was added to 1-(4-carbomethoxyphenyl)propan-2-one oxime (37.5 g) in methanol (200 ml) and the mixture refluxed for 6 hours. The reaction mixture was cooled, concentrated hydrochloric acid (100 ml) added, the mixture extracted with chloroform and the combined chloroform extracts washed with water followed by sodium bicarbonate solution. The chloroform layer was dried (MgSO4) and evaporated to give the title compound as an oil (bp 126°-129°/0.7 mm) which crystallised on standing, (mp 40°-47°). τ(CDCl3) 7.88 (3H, s), 6.28 (2H, s), 6.14 (3H, s), 2.77 (2H, d, J=8 Hz), 2,04 (2H, d, J=8 Hz).

Workup

  1. temperaturethe mixture refluxed for 6 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionthe mixture extracted with chloroform
  4. washthe combined chloroform extracts washed with water
  5. dry with materialThe chloroform layer was dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-3cf16d25ed574a5b8ed23ac7762b5f59
Source dataset
uspto-grants-1987_03
Patent number
US04654371

Reaction notes

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