4-Toluenesulfonyl chloride → Cyclobutylmethyl 4-methylbenzenesulfonate

HRID 840320Notes

Reaction equation

HRID 840320 reaction equation
[CH:1]1([CH2:5][OH:6])[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[S:14](Cl)([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15]>ClCCl>[S:14]([O:6][CH2:5][CH:1]1[CH2:4][CH2:3][CH2:2]1)([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 78130Cyclobutylcarbinol

Product 1

HCID 13163931Cyclobutylmethyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cyclobutanemethanol(5 g, 58 mmol) was dissolved in dichloromethane (150 ml) and cooled in an ice water bath. Triethylamine (10.5 ml, 75.5 mmol) was added followed by the dropwise addition of a solution of tosyl chloride (13.3 g, 69.8 mmol) in dichloromethane (50 ml). The cooling bath was removed and the mixture allowed to warm to room temperature over 16 hours. The mixture was washed with water (2×100 ml), dried (MgSO4) and concentrated in vacuo to give cyclobutanemethanol tosylate as a yellow oil which was used without further purification.

Workup

  1. temperaturecooled in an ice water bath
  2. customThe cooling bath was removed
  3. washThe mixture was washed with water (2×100 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5ce5bb6da0854086b41600bdd043ff7e
Source dataset
uspto-grants-2002_04
Patent number
US06365603B1

Reaction notes

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