Hydrochloric Acid → HCID 22854873, compound

HRID 1647952Notes

Reaction equation

HRID 1647952 reaction equation
C[O:2][C:3](=[O:20])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@@H:13]2[CH2:17][CH2:16][CH2:15][C@@H:14]2[OH:18])=[C:8]([Cl:19])[CH:7]=1)[CH3:5].[OH-].[Na+].Cl>CO>[Cl:19][C:8]1[CH:7]=[C:6]([CH:4]([CH3:5])[C:3]([OH:20])=[O:2])[CH:11]=[CH:10][C:9]=1[CH2:12][C@@H:13]1[CH2:17][CH2:16][CH2:15][C@@H:14]1[OH:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22854877HCID 22854877, compound

Product 1

HCID 22854873HCID 22854873, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3 g of methyl-2-[3-chloro-4-(cis-2-hydroxycyclopentane-1-yl methyl)phenyl]propionate were incorporated with 80 ml of an aqueous methanol containing 1.2 g of sodium hydroxide and then refluxed under heat for two hours. After the end of the reaction, the reaction mixture was treated to concentrate the solvent at a reduced pressure, incorporated with 50 ml of water and washed with 50 ml of ethyl acetate, after which the aqueous layer obtained was adjusted to a pH of 2 with conc. hydrochloric acid. The aqueous layer so adjusted was extracted with 50 ml of ethyl acetate, washed with water, dried and then freed of the solvent to obtain a residue. The thus obtained residue was adsorbed onto a silica gel-packed column and then eluted with chloroform-methanol (10:1) to obtain 2.3 g (yield 80%) of oily 2-[3-chloro-4-(cis-2-hydroxycyclopentane-1-yl methyl)phenyl] propionic acid.

Workup

  1. temperaturerefluxed
  2. temperatureunder heat for two hours
  3. customAfter the end of the reaction
  4. additionthe reaction mixture was treated
  5. concentrationto concentrate the solvent at a reduced pressure
  6. washincorporated with 50 ml of water and washed with 50 ml of ethyl acetate
  7. customafter which the aqueous layer obtained
  8. extractionThe aqueous layer so adjusted was extracted with 50 ml of ethyl acetate
  9. washwashed with water
  10. customdried
  11. customto obtain a residue
  12. washeluted with chloroform-methanol (10:1)

Sources & evidence

ORD record
ord-38808a8d4c97405ca3de03aa8ec9adff
Source dataset
uspto-grants-1995_07
Patent number
US05434292

Reaction notes

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