Isobutane → 3-(1,1,2,3,3,3-Hexafluoropropyl)cyclohex-1-ene

HRID 1414930Notes

Reaction equation

[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[F:7][C:8]([F:15])([F:14])[C:9]([F:13])=[C:10]([F:12])[F:11].CC(C)C>>[F:11][C:10]([CH:1]1[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1)([F:12])[CH:9]([F:13])[C:8]([F:15])([F:14])[F:7]

Participants

Reactant 3

HCID 6360Isobutane

HCID 8079Cyclohexene2×

HCID 8302Hexafluoropropylene

Product 1

HCID 214860713-(1,1,2,3,3,3-Hexafluoropropyl)cyclohex-1-eneYield 63%

Procedure

Cyclohexene (2.8 g., 34.2 mmole) and hexafluoropropene (1.71 g., 11.4 mmole), heated at 320° for 4 days in a Pyrex ampoule gave: (i) hexafluoropropene (0.06 g., 0.40 mmole; 4% recovery), (ii) cyclohexene (1.9 g., 23.2 mmole; 67% recovery), b.p. 83°, (iii) a liquid mixture (2.5 g.), b.r. 50°-110°/13 mm. Hg., from which was isolated (preparative g. l. c.) 3-(1,1,2,3,3,3-hexafluoropropyl)-cyclohexene (1.6 g., 6.9 mmole; 63% based on C3F6 consumed). Found: C, 47.0; H, 4.3; F, 48.5%; M (mass spectrometry), 232. C9H10F6 requires C, 46.6; H, 4.3; F, 49.1%; M, 232, b.p. 160°-161° C.

Workup

customgave
custom50°-110°/13 mm. Hg

Sources & evidence

ORD record: ord-72fa7c6d34b843d7892146bf9b4b4bb7
Source dataset: uspto-grants-1977_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04002810

Reaction notes

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