Sodium Hydroxide → HCID 20066954, compound

HRID 358613Notes

Reaction equation

HRID 358613 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([CH3:25])([CH3:24])[C:19]([O:21]CC)=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([CH3:25])([CH3:24])[C:19]([OH:21])=[O:20])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20066943HCID 20066943, compound

Product 1

HCID 20066954HCID 20066954, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 8-(4-chlorobenzenesulphonamido)-2,2-dimethyloctanoate (1.0 g), sodium hydroxide (1.5 g) in ethanol (40 ml) and water (5 ml) was stirred at room temperature for 90 hours then refluxed for 3 hours. The solvent was removed and the residue was dissolved in dilute hydrochloric acid, the resulting solution then being extracted with chloroform (3×50 ml). The combined chloroform extracts were dried over magnesium sulphate, the solvent was removed and the residue was recrystallised from isopropanol-water to give the title compound as a white solid (0.7 g) m.p. 95°-96° C.

Workup

  1. temperaturethen refluxed for 3 hours
  2. customThe solvent was removed
  3. dissolutionthe residue was dissolved in dilute hydrochloric acid
  4. extractionthe resulting solution then being extracted with chloroform (3×50 ml)
  5. dry with materialThe combined chloroform extracts were dried over magnesium sulphate
  6. customthe solvent was removed
  7. customthe residue was recrystallised from isopropanol-water

Sources & evidence

ORD record
ord-57c62dbe1bdb4bb88e1dd81777a0fd27
Source dataset
uspto-grants-1991_03
Patent number
US04997847

Reaction notes

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