Hydrochloric Acid → Methyl 2-(4-(2-oxopropyl)phenoxy)acetate

HRID 1758985Notes

Reaction equation

HRID 1758985 reaction equation
S(S([O-])=O)([O-])(=O)=[O:2].[Na+].[Na+].[C:10]([CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](=NO)[CH3:24])=[CH:18][CH:17]=1)([O:12][CH3:13])=[O:11].Cl>O.CO>[C:10]([CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](=[O:2])[CH3:24])=[CH:18][CH:17]=1)([O:12][CH3:13])=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 656671Sodium PyrosulfiteHCID 867384661-(4-Carbomethoxymethoxyphenyl)propan-2-one oxime

Product 1

HCID 13851156Methyl 2-(4-(2-oxopropyl)phenoxy)acetate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium metabisulphite (26 g) in water (60 ml) was added to 1-(4-carbomethoxymethoxyphenyl)propan-2-one oxime (7.5 g) in methanol (50 ml) and the mixture refluxed for 6 hours. The reaction mixture was cooled, concentrated hydrochloric acid (30 ml) added and the mixture extracted with ethyl acetate. The combined ethyl acetate extracts were washed with water followed by sodium bicarbonate solution. The ethyl acetate layer was dried (MgSO4) and evaporated to give the title compound as an oil which crystallised on standing, (mp 63°-70°l ). τ (CDCl3) 7.91 (3H, s), 6.30 (2H, s), 6.26 (3H, s), 5.42 (2H, s), 3.17 (2H, d, J=8 Hz), 2.87 (2H, d, J=8 Hz).

Workup

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

Sources & evidence

ORD record
ord-79ef9a6af00d412fb24e917f96ff718c
Source dataset
uspto-grants-1982_07
Patent number
US04338333

Reaction notes

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