Sodium Hydroxide → HCID 21433607, compound

HRID 2398810Notes

Reaction equation

HRID 2398810 reaction equation
C([O:3][C:4](=[O:20])[CH2:5][CH2:6][CH:7]1[CH:12]([OH:13])[CH2:11][CH2:10][CH:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8]1)C.[OH-].[Na+]>CO>[OH:13][CH:12]1[CH2:11][CH2:10][CH:9]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:8][CH:7]1[CH2:6][CH2:5][C:4]([OH:20])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53701469HCID 53701469, compound

Product 1

HCID 21433607HCID 21433607, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.68 g. (0.0025 M) of ethyl-4-hydroxy-1-phencyclohexane-3-propionate(g) (obtained in Example 4A) and 1 ml. of 50% sodium hydroxide in 10 ml. of methanol is heated at reflux for about 20 hours. Most of the solvent is removed under vacuum and the residue dissolved in water. The aqueous solution is washed with ether and made acidic with concentrated hydrochloric acid. A solid precipitate is collected on a filter and recrystallized from benzene to give 0.44 g. (71% yield) of 4-hydroxy-1-phenylcyclohexane-3-propionic acid (h) having a melting point of 153.5° to 155° C.

Workup

  1. temperatureat reflux for about 20 hours
  2. customMost of the solvent is removed under vacuum
  3. dissolutionthe residue dissolved in water
  4. washThe aqueous solution is washed with ether
  5. customA solid precipitate is collected on
  6. filtrationa filter
  7. customrecrystallized from benzene
  8. customto give 0.44 g

Sources & evidence

ORD record
ord-dcd50fa724cf4e119e8722290ded3e5d
Source dataset
uspto-grants-1977_05
Patent number
US04025558

Reaction notes

Loading…