Ethylene Glycol → 1-[p-(2-Thenoyl)phenyl]cyclopropanecarboxylic acid

HRID 1439593Notes

Reaction equation

HRID 1439593 reaction equation
[C:1]1([C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3([C:17]#N)[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1.[OH-:19].[K+].C(O)CO.C.[OH2:26]>>[C:1]1([C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3([C:17]([OH:26])=[O:19])[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 5

HCID 174Ethylene GlycolHCID 297MethaneHCID 962WaterHCID 14797Potassium HydroxideHCID 122329781-[p-(2-Thenoyl)phenyl]cyclopropanecarbonitrile

Product 1

HCID 122329791-[p-(2-Thenoyl)phenyl]cyclopropanecarboxylic acid

Conditions

Temperature
140 °C

Procedure

A mixture of 10 parts of 1-[p-(2-thenoyl)phenyl]cyclopropanecarbonitrile, 3.92 parts of potassium hydroxide, 35 parts of ethylene glycol and 3.5 parts of water is stirred for 48 hours while heating at 140° C. The reaction mixture is poured onto water, stirred with activated charcoal and filtered over hyflo. The filtrate is acidified with hydrochloric acid and the product is extracted with ether. The latter is washed with water, dried, filtered and evaporated. The solid residue is crystallized from acetonitrile, yielding 6.1 parts of 1-[p-(2thenoyl)phenyl]cyclopropanecarboxylic acid; mp. 165.9° C (dec.).

Workup

  1. additionThe reaction mixture is poured onto water
  2. filtrationfiltered over hyflo
  3. extractionthe product is extracted with ether
  4. washThe latter is washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe solid residue is crystallized from acetonitrile

Sources & evidence

ORD record
ord-3910d21901e04e4cb4391a37584b14f5
Source dataset
uspto-grants-1977_11
Patent number
US04060528

Reaction notes

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