Carbon Tetrachloride → 1-Ethenyl-4-methylbenzene

HRID 2227873Notes

Reaction equation

[CH3:1][CH2:2][CH2:3][CH2:4][CH3:5].O([CH:14]1O[C@H](CO)[C@@H](O)[C@H:17](O)[C@@H:15]1O)S(C(F)(F)F)(=O)=O.[C:25](Cl)(Cl)(Cl)Cl>>[CH3:25][C:3]1[CH:4]=[CH:5][C:17]([CH:15]=[CH2:14])=[CH:1][CH:2]=1

Participants

Reactant 3

HCID 5943Carbon Tetrachloride

HCID 8003Pentane

HCID 89837350HCID 89837350, compound

Product 1

HCID 121611-Ethenyl-4-methylbenzene

Procedure

TLC Rf=0.70 (pentane); IR (CCl4) 3089 (m), 3048 (m), 3009 (s), 2962 (s), 2962 (s), 2926 (s), 2855 (s), 1628 (m), 1570 (s), 1513 (s); 1H NMR (200 MHz, CDCl3) δ2.32 (s, 3H), 2.59 (d, J=10.9, 1H), 2.56 (d, J=17.6, 1H), 6.67 (dd, J=17.5, 10.9, 1H), 7.12 (d, J=8.0, 2H), 7.29 (d, J=8.1, 2H); 13C NMR (CDCl3) δ21.2, 112.8, 126.1, 129.2, 134.8, 136.7, 137.6; LRMS (EI) 119((M+1), 11), 118 ((M+), 100), 117 (68), 91 (42); HRMS (EI) calculated for C9H10 118.0783 (M+), found 118.0777. The IR and 1H NMR matched spectral data reported by Hollywood, F. and Suschitzaky, H., Synthesis 662-665 (1982).

Workup

custom, Synthesis 662-665 (1982)

Sources & evidence

ORD record: ord-fba61f5c9772479fa092a6b548236aa0
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06414173B1

Reaction notes

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