4-Toluenesulfonyl chloride → p-Toluenesulfonate

HRID 1007062Notes

Reaction equation

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

Participants

Conditions

Temperature: 5 °C

Procedure

In 2000 ml of pyridine was dissolved 360 g of 3,6-epoxy-4-hydroxymethyl-5-(1-hydroxy-1-methylethyl)-1-cyclohexene. In a nitrogen stream, the solution was cooled at 5° C., and 400 g of p-toluenesulfonyl chloride was added thereto. The solution was stirred at the temperature for one hour and then at room temperature for 18 hours (at this stage, a corresponding monotosylate, i.e., 3,6-epoxy-4-(1-hydroxy-1-methylethyl)-5-(p-toluenesulfonyloxymethyl)-1-cyclohexene formed in the reaction system). The reaction mixture was then heated at 60° C., and stirred at the temperature for 4 hours (at this stage, pyridine served as the base to induce cyclization so that the end compound formed). After cooling, the reaction mixture was poured into a saturated sodium chloride solution, followed by extraction with ethyl acetate. The ethyl acetate solution was washed with dilute hydrochloric acid, water and an aqueous saturated potassium carbonate solution, dried over magnesium sulfate, and concentrated in vacuum. Vacuum distillation of the concentrate gave 308 g (yield 95%) of the end compound, 3,6-epoxy-2,2-dimethyl-2,2a,3,6,6a,7-hexahydrobenzo[c]furan.

Workup

waitat room temperature for 18 hours (at this stage

Sources & evidence

ORD record: ord-5443a40790b440c996009f762e341bc4
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06794111B2

Reaction notes

Loading…