Dimethyl Sulfoxide → ETHYL (1-CYANOCYCLOHEXYL)ACETATE

HRID 654290Notes

Reaction equation

HRID 654290 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4]([C:9]1([C:15]#[N:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)C(OC)=O.[Cl-].[Li+].O.[CH3:21]S(C)=O>>[CH2:1]([O:2][C:3](=[O:17])[CH2:4][C:9]1([C:15]#[N:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)[CH3:21]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962Water2×HCID 433294Lithium ChlorideHCID 21652232HCID 21652232, compound

Product 1

HCID 10965422ETHYL (1-CYANOCYCLOHEXYL)ACETATEYield 74%

Procedure

26.9 g (100 mmol) of (1-cyanocyclohexyl)malonic acid dimethyl ester, 4.3 g (100 mmol) or lithium chloride and 3.6 g (200 mmol) of water were heated in 300 ml of dimethyl sulfoxide for 22 hours to 150° C. Then it was cooled, mixed with 700 ml of water and extracted with 1000 ml of pentane. 14.4 g of (1-cyanocyclohexyl)acetic acid ethyl ester was obtained by distillation of the organic phase, corresponding to a yield of 74 percent (relative to the (1-cyanocyclohexyl) malonic acid dimethyl ester used). Data for the product was:

Workup

  1. temperatureThen it was cooled
  2. extractionextracted with 1000 ml of pentane

Sources & evidence

ORD record
ord-f7d80cd0556b49be90f3b80e5cba5be3
Source dataset
uspto-grants-1992_07
Patent number
US05130455

Reaction notes

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