Hydrochloric Acid → HCID 22854875, compound

HRID 1647951Notes

Reaction equation

HRID 1647951 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 22854879HCID 22854879, compound

Product 1

HCID 22854875HCID 22854875, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3 g of methyl-2-[3-chloro-4-(trans-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 2.4 g (yield 84%) of oily 2-[3-chloro-4-(trans-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-d9720f9faac04a58b0d0c55bb1ffdea1
Source dataset
uspto-grants-1995_07
Patent number
US05434292

Reaction notes

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