Cyclohexanone → 1-Tert-butylcyclohexan-1-ol

HRID 1261568Notes

Reaction equation

HRID 1261568 reaction equation
[C:1]([Mg]Cl)([CH3:4])([CH3:3])[CH3:2].[Li+].[Cl-].[C:9]1(=[O:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>>[C:1]([C:9]1([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 7967CyclohexanoneHCID 433294Lithium ChlorideHCID 178418310HCID 178418310, compound

Product 1

HCID 2879171-Tert-butylcyclohexan-1-ol

Procedure

According to Example 2, t-BuMgCl.LiCl (1.01 M in THF 2.18 mL; 2.20 mmol; 1.10 equiv) was reacted with cyclohexanone (178 mg; 2.00 mmol) in the presence of LaCl3.2LiCl (0.33 M; 6.06 mL, 2.00 mmol, 1.00 equiv). Column chromatographical purification (silica; pentane:Et2O, 9:1) afforded the desired product as colorless oil, which started to crystallize after being chilled, mp=49−50° C. (287 mg, 92%).

Workup

  1. customColumn chromatographical purification (silica; pentane:Et2O, 9:1)

Sources & evidence

ORD record
ord-adadbe4ae7274d8aaf56990a0b069ebd
Source dataset
uspto-grants-2013_06
Patent number
US08470982B2

Reaction notes

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