2,6-Dimethylcyclohexanone → 1,3-Dimethyl-2-methylidenecyclohexane

HRID 1589590Notes

Reaction equation

HRID 1589590 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].C[CH:7]1[CH2:12][CH2:11]C[CH:9](C)[C:8]1=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>[CH2:1]=[C:2]1[CH:12]([CH3:11])[CH2:7][CH2:8][CH2:9][CH:3]1[CH3:4]

Participants

5

Reactant 2

HCID 177802,6-DimethylcyclohexanoneHCID 178418339Butyllithium

Product 1

HCID 1406031,3-Dimethyl-2-methylidenecyclohexaneYield 48.3%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 3283Diethyl EtherSolvent

Procedure

Methyltriphenylphosphonium bromide (286 g, 0.80 mole) was suspended in ether (1500 ml) and treated with n-butyllithium (1.6M in ether; 500 ml, 0.80 mole), followed by 2,6-dimethylcyclohexanone (50.4 g, 0.40 mole), following the procedure described in Example 12, Part A. The crude product was distilled to give 1-methylene-2,6-dimethylcyclohexane (24 g), b.p. 146°-154° C./760 mm.

Workup

  1. distillationThe crude product was distilled

Sources & evidence

ORD record
ord-78daa987663f4c62bafce29129eba43a
Source dataset
uspto-grants-1986_02
Patent number
US04571345

Reaction notes

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