Diisobutylamine → 2-Chloro-4-(oxan-4-yl)phenol

HRID 843633Notes

Reaction equation

HRID 843633 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C(NCC(C)C)C(C)C.S(Cl)([Cl:26])(=O)=O>C1(C)C=CC=CC=1>[Cl:26][C:9]1[CH:8]=[C:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH:12]=[CH:11][C:10]=1[OH:13]

Participants

5

Reactant 3

HCID 8085DiisobutylamineHCID 24648Sulfuryl chloride2×HCID 227373584-(Oxan-4-yl)phenol

Product 1

HCID 184146372-Chloro-4-(oxan-4-yl)phenolYield 78.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To a 30ml Toluene solution of 4-(4-tetrahydropyranyl) phenol 1 g (5.61 mmol) and diisobutylamine 0.08 ml (0.46 mmol) was added sulfuryl chloride 0.51 ml (6.35 mmol) over 3 hr period upon heating at 70° C. Stirring was continued at that temp. for 2 hr after the addition of sulfuryl chloride was complete. The solvent was removed under reduced pressure, diluted with ethyl acetate and washed with 2N aqueous HCl, saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered, concentrated, chromatographed on silica gel (hexanes:ethyl acetate) to give 0.941 g of the title compound as while solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additiondiluted with ethyl acetate
  3. washwashed with 2N aqueous HCl, saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed on silica gel (hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-ec608eeb753c442eb155f83eb2f5a2b8
Source dataset
uspto-grants-2002_04
Patent number
US06380191B1

Reaction notes

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