Hydrochloric Acid → 3,4-(Dimethylmethylenedioxy)-2-hydroxy-5-hexen-1-yl p-toluenesulfonate

HRID 1741949Notes

Reaction equation

[CH3:1][C:2]1([CH3:13])[O:12][CH:9]([CH:10]=[CH2:11])[CH:4]([CH:5]([OH:8])[CH2:6][OH:7])[O:3]1.N1C=CC=CC=1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.Cl>C(Cl)(Cl)Cl>[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26]([O:7][CH2:6][CH:5]([OH:8])[CH:4]2[O:3][C:2]([CH3:13])([CH3:1])[O:12][CH:9]2[CH:10]=[CH2:11])(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3,4-(Dimethylmethylenedioxy)-5-hexene-1,2-diol (9.77 g) was mixed with 155 ml of pyridine and 52 ml of chloroform, and 11.39 g of p-toluenesulfonyl chloride was added gradually in four portions at 0° C. The mixture was stirred at 0° C. for 6 hours, poured into 6N hydrochloric acid with ice and extracted with diethyl ether. The extract was washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution in sequence, dried with anhydrous ride aqueous solution in sequence, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure to afford 17.88 g of 3,4-(dimethylmethylenedioxy)-2-hydroxy-5-hexen-1-yl p-toluenesulfonate having the following properties.

Workup

additionwas added gradually in four portions at 0° C
extractionextracted with diethyl ether
washThe extract was washed with a saturated sodium hydrogen carbonate aqueous solution
dry with materiala saturated sodium chloride aqueous solution in sequence, dried with anhydrous ride aqueous solution in sequence
dry with materialdried with anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-865fe2c9ba554b55ad414c429207fb1f
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05334740

Reaction notes

Loading…