Sodium Hydroxide → HCID 22854872, compound

HRID 1647949Notes

Reaction equation

HRID 1647949 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+]>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

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22854876HCID 22854876, compound

Product 1

HCID 22854872HCID 22854872, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3 g of methyl-2-[3-chloro-4-(cis-2-hydroxycyclohexane-1-yl methyl)phenyl]propionate was 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 remove the solvent therefrom at a reduced pressure, incorporated with 50 ml of water and washed with 50 ml of ethyl acetate, after which the aqueous layer was adjusted to a pH of 2 with conc. hydrochloric acid, extracted with 50 ml of ethyl acetate, washed with water, dried and then freed of the solvent thereby to obtain 2.3 g (yield 80%) of oily 2-[3-chloro-4-(cis-2-hydroxycyclohexane-1-yl methyl)phenyl]propionic acid having the following 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. customto remove the solvent
  6. washat a reduced pressure, incorporated with 50 ml of water and washed with 50 ml of ethyl acetate
  7. extractionextracted with 50 ml of ethyl acetate
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-6a571513c91243659136de7b6e8f8a80
Source dataset
uspto-grants-1995_07
Patent number
US05434292

Reaction notes

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