Sodium dichromate dihydrate → HCID 14536426, compound

HRID 345760Notes

Reaction equation

HRID 345760 reaction equation
[OH2:1].O.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].[C:14]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]([CH3:26])[CH3:25])[C:19]=1[OH:27])([CH3:17])([CH3:16])[CH3:15]>S(=O)(=O)(O)O.O.C(OCC)C>[C:14]([C:18]1[C:19](=[O:27])[C:20]([CH:24]([CH3:25])[CH3:26])=[CH:21][C:22](=[O:1])[CH:23]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 2

HCID 108005Sodium dichromate dihydrateHCID 1409602-Isopropyl-6-tert-butylphenol

Product 1

HCID 14536426HCID 14536426, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

A 160 g quantity of sodium dichromate dihydrate was dissolved in a mixture of 100 ml of 97% sulfuric acid and 230 ml of water, and the solution was added to a solution of 45.0 g of 2-tert-butyl-6-isopropylphenol in 350 ml of diethyl ether with stirring at a temperature of 5°-10° C. over a period of 2.5 hours. The reaction mixture was poured into water and extracted with diethyl ether. The organic layer was washed serially with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated. The resulting crude product was purified by silica gel column chromatography (eluent: diethyl ether-hexane=1:10), giving 12.7 g of the title compound as a pale yellow oil.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic layer was washed serially with a saturated aqueous solution of sodium bicarbonate
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resulting crude product was purified by silica gel column chromatography (eluent: diethyl ether-hexane=1:10)

Sources & evidence

ORD record
ord-ba499c572f2f440fb56a2d9236d46400
Source dataset
uspto-grants-1991_10
Patent number
US05059598

Reaction notes

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