Toluene → HCID 86626446, compound

HRID 421002Notes

Reaction equation

[C:1]([CH:4]([CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])[CH2:5][OH:6])([CH3:3])=[CH2:2].C1(C)C=CC=CC=1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>O>[CH3:26][S:27]([O:6][CH2:5][CH:4]([C:1]([CH3:3])=[CH2:2])[CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])(=[O:29])=[O:28]

Participants

Conditions

Temperature: 5 °C

Procedure

2-Isopropenyl-5-methyl-4-hexen-1-ol (154.25 g, 1.00 mol), toluene (775.6 g) and triethylamine (122.5 g, 1.21 mol) were charged in a four-neck flask (inner volume 2 L) equipped with a thermometer, a stirrer and a dropping funnel, and the mixture was cooled to 5° C. Then, methanesulfonyl chloride (137.5 g, 1.20 mol) was added dropwise to this mixture over 30 min. After the completion of the dropwise addition, the reaction mixture was further stirred at 25° C. for 1 hr. Water (462.4 g) was added to the obtained reaction mixture, the mixture was stirred for 15 min, and the organic layer was separated. The obtained organic layer was washed with 5 mass % aqueous solution of sodium hydrogencarbonate (488.0 g) and water (464.1 g) and concentrated to give 2-isopropenyl-5-methyl-4-hexen-1-yl methanesulfonate (237.73 g, 0.972 mol, yield 97.2%, purity 95%). The result of 1H-NMR measurement of 2-isopropenyl-5-methyl-4-hexen-1-yl methanesulfonate is shown below. The present compound is a novel substance.

Workup

customequipped with a thermometer, a stirrer and a dropping funnel
additionAfter the completion of the dropwise addition
stirringthe mixture was stirred for 15 min
customthe organic layer was separated
washThe obtained organic layer was washed with 5 mass % aqueous solution of sodium hydrogencarbonate (488.0 g) and water (464.1 g)
concentrationconcentrated

Sources & evidence

ORD record: ord-90f0cc2bb6134c85acbeb5b9fd9867d6
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097746B2

Reaction notes

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