4-tert-Butylcyclohexanol → HCID 12602932, compound

HRID 1262898Notes

Reaction equation

HRID 1262898 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>N1C=CC=CC=1>[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([O:11][CH:8]2[CH2:7][CH2:6][CH:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:10][CH2:9]2)(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 73914-tert-ButylcyclohexanolHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 12602932HCID 12602932, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Into a one liter, four-necked, round bottom flask equipped with stirrer, condenser, and thermometer, 200.0 parts of pyridine and 31.75 parts of 4-t-butylcyclohexanol were mixed under a nitrogen blanket and chilled to 0° C. with an ice water bath. To this solution 47.75 parts of p-toluenesulfonyl chloride were added in portions over thirty minutes. The solution was stirred for one hour at 0° C. and then allowed to stand for twenty-four hours at 15° C. The mixture was poured into one liter of ice water and subsequently extracted with 700 parts of methylene chloride. The organic layer was washed successively with cold 6 N sulfuric acid (until the water layer was acidic to pH paper), dilute sodium bicarbonate (three times with 500 part-portions), and water (twice with 500 part-portions). It was then dried over sodium sulfate, filtered, and the solvent removed in vacuo to yield the 4-t-butylcyclohexyl para-toluenesulfonate as a pale yellow liquid which solidified on standing.

Workup

  1. customInto a one liter, four-necked, round bottom flask equipped with stirrer, condenser
  2. waitto stand for twenty-four hours at 15° C
  3. extractionsubsequently extracted with 700 parts of methylene chloride
  4. washThe organic layer was washed successively with cold 6 N sulfuric acid (until the water layer
  5. dry with materialIt was then dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-239ee640c1b642a292c2dac5f27e3069
Source dataset
uspto-grants-1984_06
Patent number
US04454274

Reaction notes

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