Hydrochloric Acid → HCID 22854874, compound

HRID 1647948Notes

Reaction equation

HRID 1647948 reaction equation
C[O:2][C:3](=[O:21])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]2[OH:19])=[C:8]([Cl:20])[CH:7]=1)[CH3:5].[OH-].[Na+].Cl>CO>[Cl:20][C:8]1[CH:7]=[C:6]([CH:4]([CH3:5])[C:3]([OH:21])=[O:2])[CH:11]=[CH:10][C:9]=1[CH2:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[OH:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22854878HCID 22854878, compound

Product 1

HCID 22854874HCID 22854874, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3 g of methyl-2-[3-chloro-4-(trans-2-hydroxycyclohexane-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 recrystallized from isopropyl ether thereby to obtain 2.5 g (yield of 2-[3-chloro-4-(trans-2-hydroxycyclohexane-1-yl methyl)phenyl]propionic acid having the following melting point and instrumental analyses.

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. customThe thus obtained residue was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-28d9d3af91d649a589f6ebb141e87e62
Source dataset
uspto-grants-1995_07
Patent number
US05434292

Reaction notes

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