Sulfuric Acid → HCID 12422094, compound

HRID 1606739Notes

Reaction equation

HRID 1606739 reaction equation
C([O:3]CC)C.[Cl:6][C:7]1[CH:26]=[CH:25][C:10]([CH2:11][C:12]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:13]=2[CH2:14][CH2:15][CH2:16][CH:17]3[C:22]([OH:24])=[O:23])=[CH:9][CH:8]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].S(=O)(=O)(O)O>O>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([C:12]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:13]=2[CH2:14][CH2:15][CH2:16][CH:17]3[C:22]([OH:24])=[O:23])=[O:3])=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 25408Sodium DichromateHCID 20310108HCID 20310108, compound

Product 1

HCID 12422094HCID 12422094, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 200 ml. of ethyl ether is added 15 g. of 5-(p-chlorobenzyl)-1,2,3,4-tetrahydro-1-naphthoic acid, and a solution of 5 g. of sodium dichromate in 24 ml. of 6N sulfuric acid is added dropwise. After stirring overnight, 100 ml. of water is added and the ethereal layer is further 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 with chloroform as the eluent and, then, recrystallized from benzene. The described procedure gives 5-(p-chlorobenzoyl)-1,2,3,4-tetrahydro-1-naphthoic acid, melting point: 152.5°-153.5°C.

Workup

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

Sources & evidence

ORD record
ord-feb0072fa7904629b17daf2aa7ffebe9
Source dataset
uspto-grants-1976_04
Patent number
US03953500

Reaction notes

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