Methanol → Methyl alpha-methylbenzeneacetate

HRID 2289133Notes

Reaction equation

HRID 2289133 reaction equation
[CH3:1][O-:2].[Na+].C(C1[C:10]2[CH:11]=[CH:12][C:13](OCCCBr)=[C:14]([CH2:15][CH2:16]C)[C:9]=2ON=1)C.[CH3:23][OH:24]>>[CH3:1][O:2][C:23](=[O:24])[CH:15]([C:14]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH3:16]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 10942334Sodium MethoxideHCID 69968236HCID 69968236, compound

Product 1

HCID 569653Methyl alpha-methylbenzeneacetate

Procedure

A solution of 2-(3-chloro-4-dimethylcarbamoylthio)phenyl propionic acid methyl ester (0.106 g; 0.352 mmol) in dry methanol (1.42 mL) was treated with a solution of sodium methoxide in methanol (4.37 M; 0.113 mL; 0.493 mmol). The solution was refluxed for 4 hours and then cooled to room temperature. 3-ethyl-6-(3-bromopropyl)oxy-7-propyl-benz[4,5]isox-azole (0.096 grams; 0.293 mmol) was added and the reaction stirred for 1 hour. The reaction mixture was partitioned between isopropyl acetate and pH 4.0 buffer. The organic layer was dried over magnesium sulfate, filtered and evaporated. Silica gel chromatography afforded the title compound.

Workup

  1. temperatureThe solution was refluxed for 4 hours
  2. customThe reaction mixture was partitioned between isopropyl acetate and pH 4.0 buffer
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-ea3f269064f8435eabf52763a04f74bb
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

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