2-tert-Butylcyclohexanone → HCID 13449626, compound

HRID 1589591Notes

Reaction equation

HRID 1589591 reaction equation
[CH2:1]([Li])CCC.[C:6]([CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]1=O)([CH3:9])([CH3:8])[CH3:7]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>[CH2:1]=[C:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH:10]1[C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 2

HCID 1026812-tert-ButylcyclohexanoneHCID 178418339Butyllithium

Product 1

HCID 13449626HCID 13449626, compoundYield 44.6%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 3283Diethyl EtherSolvent

Procedure

Methyltriphenylphosphonium bromide (346 g, 0.97 mole) was suspended in ether (1500 ml) and treated with n-butyllithium (2.5M in ether; 388 ml, 0.97 mole), followed by 2-t-butylcyclohexanone (50 g, 0.324 mole), following the procedure described in Example 12, Part A. The reaction mixture was heated under reflux for 2 days and then worked up in the usual manner. The crude product was fractionated to provide methylene-2-t-butylcyclohexane (22 g), which was pure by GC.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 days

Sources & evidence

ORD record
ord-86330b233f974d9c936d1c0d41f2eced
Source dataset
uspto-grants-1986_02
Patent number
US04571345

Reaction notes

Loading…