Ethylene Glycol → HCID 68469081, compound

HRID 502944Notes

Reaction equation

HRID 502944 reaction equation
[OH-:1].[K+].C(O)C[OH:5].[Cl:7][C:8]1[C:12]([CH3:13])=[CH:11][S:10][C:9]=1[C:14]1([C:19]#N)[CH2:18][CH2:17][CH2:16][CH2:15]1.CCOCC>O>[Cl:7][C:8]1[C:12]([CH3:13])=[CH:11][S:10][C:9]=1[C:14]1([C:19]([OH:5])=[O:1])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 3283Diethyl EtherHCID 14797Potassium HydroxideHCID 68469844HCID 68469844, compound

Product 1

HCID 68469081HCID 68469081, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

Potassium hydroxide (1.36 g) was added to an ethylene glycol (20 ml) solution of 1-(3-chloro-4-methyl-2-thienyl)cyclopentanecarbonitrile and the whole was stirred at 190° C. for 2 hours. After the reaction solution and ether were added to water, the aqueous layer was separated. An 1M aqueous hydrochloric acid solution was added to the aqueous layer to acidify the liquid and, after ether was added, the organic layer was separated. The layer was dried over anhydrous sodium sulfate and filtered and then the solvent was removed by evaporation under reduced pressure to obtain 1.59 g of 1-(3-chloro-4-methyl-2-thienyl)cyclopentanecarboxylic acid (pale brown solid).

Workup

  1. customthe aqueous layer was separated
  2. additionAn 1M aqueous hydrochloric acid solution was added to the aqueous layer
  3. additionafter ether was added
  4. customthe organic layer was separated
  5. dry with materialThe layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-bab20b0c545f49e899a3480963be835c
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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