Sulfuric Acid → HCID 12422093, compound

HRID 1606738Notes

Reaction equation

HRID 1606738 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:23]=[CH:22][C:7]([CH2:8][C:9]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[CH2:11][CH2:12][CH2:13][CH:14]3[C:19]([OH:21])=[O:20])=[CH:6][CH:5]=1.[Mn]([O-])(=O)(=O)=[O:25].[K+].S(=O)(=O)(O)O.S(=O)(O)[O-].[Na+]>O>[C:4]1([CH3:3])[CH:5]=[CH:6][C:7]([C:8]([C:9]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[CH2:11][CH2:12][CH2:13][CH:14]3[C:19]([OH:21])=[O:20])=[O:25])=[CH:22][CH:23]=1

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 12422125HCID 12422125, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 12422093HCID 12422093, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 200 ml. of 1N aqueous sodium hydroxide is dissolved 14 g. of 5-(p-methylbenzyl)-1,2,3,4-tetrahydro-1-naphthoic acid, and a solution of 26 g. of potassium permanganate in 800 ml. of water is added dropwise. After stirring overnight, the reaction mixture is rendered acidic by the addition of concentrated sulfuric acid, followed by the addition of sodium bisulfite. The mixture is extracted with chloroform and the chloroform layer is washed with water and dried over anhydrous magnesium sulfate. The solvent is distilled off under reduced pressure and the oily residue is purified by column chromatography on silica gel equilibrated with oxalic acid and, then, recrystallized from cyclohexane. The described procedure gives 5-(p-toluoyl)-1,2,3,4-tetrahydro-1-naphthoic acid, melting point: 102°-103°C.

Workup

  1. extractionThe mixture is extracted with chloroform
  2. washthe chloroform layer is washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent is distilled off under reduced pressure
  5. customthe oily residue is purified by column chromatography on silica gel
  6. customrecrystallized from cyclohexane

Sources & evidence

ORD record
ord-55e1f0396b90412aa39b962bdd4b9d90
Source dataset
uspto-grants-1976_04
Patent number
US03953500

Reaction notes

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