Sulfuric Acid → HCID 12422094, compound

HRID 436176Notes

Reaction equation

HRID 436176 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-1052a75bc3a947cdace615e09a266744
Source dataset
uspto-grants-1977_02
Patent number
US04007225

Reaction notes

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