4-Toluenesulfonyl chloride → HCID 86755686, compound

HRID 381779Notes

Reaction equation

HRID 381779 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@:9]2([OH:16])[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[OH:15])=[CH:5][CH:4]=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23]([O:15][C@H:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C@:9]2([OH:16])[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 70210841HCID 70210841, compound

Product 1

HCID 86755686HCID 86755686, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

[1S*,2S*]-1-(4-methoxyphenyl)cyclohexane-1,2-diol (2.02 g, 9.1 mmole, prepared in Part A above) was dissolved in pyridine (25 mL) and cooled in ice bath, then p-toluenesulfonyl chloride (2.71 g, 14.3 mmole) was added in portions. The resultant orange solution was allowed to warm to ambient temperature over a period of about 1 hours, stirred at ambient temperature overnight, and then added slowly to ice-water with stirring. The resultant gray solids were filtered and dried to yield the desired crude product (1.073 g). Recrystallization from benzene/petroleum ether gave the purified product as pale straw-colored plates.(0.88 g, 0.23 mmole, 25% yield based upon the diol starting material). Treatment of a saturated benzene solution of this purified product with charcoal and recrystallization by addition of petroleum ether to the benzene solution resulted in a product in the form of white plates.

Workup

  1. temperaturecooled in ice bath
  2. stirringwith stirring
  3. filtrationThe resultant gray solids were filtered
  4. customdried

Sources & evidence

ORD record
ord-daa82000f0d343f1bccc50aba18e6dbd
Source dataset
uspto-grants-2001_10
Patent number
US06307085B1

Reaction notes

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