Methanol → Methyl 1-(mercaptomethyl)cyclopropaneacetate

HRID 2259487Notes

Reaction equation

HRID 2259487 reaction equation
C([S:4][CH2:5][C:6]1([CH2:9][C:10]#N)[CH2:8][CH2:7]1)(=O)C.[OH2:12].OS(O)(=O)=O.[CH3:18][OH:19]>>[SH:4][CH2:5][C:6]1([CH2:9][C:10]([O:19][CH3:18])=[O:12])[CH2:7][CH2:8]1

Participants

5

Reactant 4

HCID 887MethanolHCID 962Water2×HCID 1118Sulfuric AcidHCID 117896201-(Acetylthiomethyl)cyclopropaneacetonitrile

Product 1

HCID 15288152Methyl 1-(mercaptomethyl)cyclopropaneacetateYield 93%

Conditions

Temperature
25 °C

Procedure

To a solution of the nitrile of Step 8 (45 g, 266 mmol) in MeOH (1.36 L) was added H2O(84 mL) and conc. H2SO4 (168 mL). The mixture was heated to reflux for 20 hr, cooled to 25° C., H2O(1 L) was added and the product was extracted with CH2Cl2 (2×1.5 L). The organic extract was washed with H2O and dried over Na2SO4. Concentration of the organic solution gave 36 g (93%) of the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 20 hr
  3. extractionthe product was extracted with CH2Cl2 (2×1.5 L)
  4. extractionThe organic extract
  5. washwas washed with H2O
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-3561463f2f1f44499b54b2448ade42d8
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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