Hydrochloric Acid → 2-[4-(2-Hydroxycyclopentylidenemethyl)phenyl]propionic acid

HRID 1462935Notes

Reaction equation

HRID 1462935 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][C:3]1=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1.C([BH3-])#N.[Na+].Cl>CO>[OH:1][CH:2]1[CH2:6][CH2:5][CH2:4][C:3]1=[CH:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 540467252-(4-((2-Oxocyclopentylidene)methyl)phenyl)propanoic acid

Product 1

HCID 544482712-[4-(2-Hydroxycyclopentylidenemethyl)phenyl]propionic acidYield 64.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

123 mg of 2-[4-(2-oxocyclopentylidenemethyl)phenyl]propionic acid (which can be prepared as described in United Kingdom Patent Specification No. 2,002,762) and 75 mg of sodium cyanoborohydride were dissolved in 5 ml of methanol. The pH of the solution was adjusted to a value of 3 by the addition of 6N hydrochloric acid, whilst ice-cooling. The mixture was stirred under reflux for 40 minutes, after which it was diluted with ice-water and then extracted with diethyl ether. The extract was washed with water and then the solvent was distilled off to give crystals. These were recrystallised from a 1:1 by volume mixture of ethyl acetate and hexane, to give 80 mg of the title compound, melting at 125°-132° C.

Workup

  1. temperaturecooling
  2. temperatureunder reflux for 40 minutes
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with water
  5. distillationthe solvent was distilled off
  6. customto give crystals
  7. customThese were recrystallised from a 1:1 by volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-f15091ef3cd14eaebb2c675019cc1465
Source dataset
uspto-grants-1984_07
Patent number
US04461912

Reaction notes

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