Ethylene Glycol → 4-(4-Fluorophenyl)-4-methoxy-1-phenylcyclohexanecarboxylic acid

HRID 657495Notes

Reaction equation

HRID 657495 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:22][CH3:23])[CH2:13][CH2:12][C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:14]#N)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-:24].[K+].C(O)C[OH:28]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:22][CH3:23])[CH2:13][CH2:12][C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:14]([OH:28])=[O:24])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 594425494-(4-Fluorophenyl)-4-methoxy-1-phenylcyclohexanecarbonitrile

Product 1

HCID 251027964-(4-Fluorophenyl)-4-methoxy-1-phenylcyclohexanecarboxylic acid

Conditions

Temperature
200 °C

Procedure

500 mg of 4-(4-fluorophenyl)-4-methoxy-1-phenylcyclohexanecarbonitrile were dissolved in 30 ml of ethylene glycol and 272 mg of potassium hydroxide were added. The reaction mixture was subsequently stirred for 5 h at 200° C. After cooling, the reaction mixture was poured onto an ice/water mixture and extracted three times with MTB. The aqueous phase was acidified to pH=1 with 2 N hydrochloric acid. The precipitated crude product was filtered off with suction and dissolved in a little hot toluene. The crystals deposited during cooling were filtered off with suction and dried. 450 mg of the title compound were obtained as a white solid.

Workup

  1. temperatureAfter cooling
  2. extractionextracted three times with MTB
  3. customThe precipitated crude product
  4. filtrationwas filtered off with suction
  5. dissolutiondissolved in a little hot toluene
  6. temperatureduring cooling
  7. filtrationwere filtered off with suction
  8. customdried

Sources & evidence

ORD record
ord-7d9061ae9c6849548e28b7ce8d214411
Source dataset
uspto-grants-2011_12
Patent number
US08076324B2

Reaction notes

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