Sulfuryl chloride → HCID 22390446, compound

HRID 991585Notes

Reaction equation

HRID 991585 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.S(Cl)([Cl:19])(=O)=O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:19][C:12]1[CH:13]=[C:8]([CH:5]2[CH2:6][CH2:7][C:2]([CH3:15])([CH3:1])[CH2:3][CH2:4]2)[CH:9]=[CH:10][C:11]=1[OH:14]

Participants

6

Reactant 3

HCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 22737361HCID 22737361, compound

Product 1

HCID 22390446HCID 22390446, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(4,4-dimethylcyclohexyl)phenol (2.16 g, 10.6 mmol), disiobutylamine (0.14 mL) and sulfuryl chloride (0.59 mL, 7.4 mmol) in toluene was stirred at 70° C. for 2 h. The reaction mixture was cooled to room temperature, treated with saturated aqueous sodium bicarbonate and diluted with ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated in vacuo. The resulting oil was subjected to chromatography on silica gel, using hexane/ethyl acetate (20:1), to afford the title compound (1.7 g).

Workup

  1. washThe organic layer was washed with water, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c3f109239d72487598731cc2061e06b1
Source dataset
uspto-grants-2002_10
Patent number
US06465497B2

Reaction notes

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