Sodium Hydroxide → HCID 13338866, compound

HRID 1285395Notes

Reaction equation

HRID 1285395 reaction equation
[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:23]=[CH:22][C:16]([C:17]([O:19]CC)=[O:18])=[CH:15][C:14]=2[Cl:24])=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:23]=[CH:22][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=2[Cl:24])=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13338862HCID 13338862, compound

Product 1

HCID 13338866HCID 13338866, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 4-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)propoxy]-3-chlorobenzoate (1.0 g), ethanol (10 ml) and 1N sodium hydroxide (10 ml) was refluxed for 0.5 hour, then concentrated, acidified with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water, dried over sodium sulfate and concentrated, and the crystals were collected by filtration. There was obtained 4-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)propoxy]-3-chlorobenzoic acid as needles (840 mg). Melting point 171°-172° C.

Workup

  1. temperaturewas refluxed for 0.5 hour
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-fd92ae6d627b48d486decd2a5ca9d89e
Source dataset
uspto-grants-1986_01
Patent number
US04567201

Reaction notes

Loading…