Water → 2,2-Dimethyl-3-methylthiocyclopropane-1-carboxylic acid methyl ester

HRID 1680801

Reaction equation

HRID 1680801 reaction equation
[CH3:1][O:2][C:3]([C:5]1(C(OC)=O)[CH:7]([CH3:8])[C:6]1([CH3:10])[CH3:9])=[S:4].O.[Br-].[Na+]>O=P1(C)CCC=C1>[CH3:1][O:2][C:3]([CH:5]1[CH:7]([CH3:8])[C:6]1([CH3:10])[CH3:9])=[S:4]

Participants

5

Reactant 3

HCID 962Water2×HCID 253881Sodium BromideHCID 887684162,2-Dimethyl-3-methylthio-cyclopropane-1,1-dicarboxylic acid dimethyl ester

Product 1

HCID 887707122,2-Dimethyl-3-methylthiocyclopropane-1-carboxylic acid methyl esterYield 75.8%

Reagents, catalysts & solvents 1

HCID 701042,3-Dihydro-1-methyl-1H-phosphole 1-oxideSolvent

Procedure

23 g (0.1 mol) of 2,2-dimethyl-3-methylthio-cyclopropane-1,1-dicarboxylic acid dimethyl ester (prepared according to J. Chem. Soc., Chem. Comm. 1972 (7), 375) were dissolved in 25 ml of 1-oxo-1-methylphospholine and 2 ml of water and the solution was heated to 180° C. with 8 g of sodium bromide for 12 hours. The mixture was then cooled, poured into water, extracted by shaking with toluene and distilled. 12 g (=69% of theory) of 2,2-dimethyl-3-methylthiocyclopropane-1-carboxylic acid methyl ester of boiling point 75° C./3 mm Hg are obtained.

Workup

  1. temperatureThe mixture was then cooled
  2. extractionextracted
  3. distillationdistilled

Sources & evidence

ORD record
ord-6e4dea2e83f2409fa9d9c2d84f8eb01f
Source dataset
uspto-grants-1981_06
Patent number
US04276225

Linked notes

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