Potassium Hydroxide → HCID 21418533, compound

HRID 596341Notes

Reaction equation

HRID 596341 reaction equation
[CH3:1][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][NH:24][C:25](=[O:34])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)([CH3:8])[C:3]([O:5]CC)=[O:4].[OH-].[K+]>O.CO>[CH3:8][C:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][NH:24][C:25](=[O:34])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])=[CH:18][CH:17]=2)=[CH:14][CH:15]=1)([CH3:1])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 21418532HCID 21418532, compound

Product 1

HCID 21418533HCID 21418533, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4gm (8.6 millimols) of ethyl 2-methyl-2-{4-[2-(2-methoxy-benzamido)-ethyl]-biphenyl-4'-oxy}-propionate were hydrolized at room temperature over a period of 12 hours with a solution of 1gm (17.2 millimols) of potassium hydroxide in 5 ml of water and 95 ml of methanol. After distilling off the methanol, 100 ml of water were added, and the mixture was extracted with ether. The pH of the aqueous phase was adjusted to between 1 and 2 with 2 N hydrochloric acid, and the acid mixture was extracted with chloroform. The combined chloroform extracts were dried over sodium sulfate and evaporated to dryness, and the residue was recrystallized from ether. Yield: 3.2 gm (86% of theory); m.p. 133° C.

Workup

  1. distillationAfter distilling off the methanol, 100 ml of water
  2. additionwere added
  3. extractionthe mixture was extracted with ether
  4. extractionthe acid mixture was extracted with chloroform
  5. dry with materialThe combined chloroform extracts were dried over sodium sulfate
  6. customevaporated to dryness
  7. customthe residue was recrystallized from ether

Sources & evidence

ORD record
ord-4bc9fc69f851459b811e0fab75bdea0e
Source dataset
uspto-grants-1977_03
Patent number
US04010279

Reaction notes

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