Camphor → 2-Bornanol, 2-phenyl-

HRID 1261569Notes

Reaction equation

HRID 1261569 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[Cl-].[CH3:11][C:12]12[C:18]([CH3:20])([CH3:19])[CH:15]([CH2:16][CH2:17]1)[CH2:14][C:13]2=[O:21]>>[CH3:11][C:12]12[C:18]([CH3:20])([CH3:19])[CH:15]([CH2:16][CH2:17]1)[CH2:14][C:13]2([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[OH:21]

Participants

4

Reactant 3

HCID 2537CamphorHCID 433294Lithium ChlorideHCID 178418255HCID 178418255, compound

Product 1

HCID 5776042-Bornanol, 2-phenyl-

Procedure

According to Example 2, PhMgBr.LiCl (1.00 M in THF; 1.10 mL; 1.10 mmol; 1.10 equiv) was reacted with 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (152 mg; 1.00 mmol) in the presence of LaCl3.2LiCl (0.33 M; 3.03 mL, 1.00 mmol, 1.00 equiv). Column chromatographical purification (silica; pentane:Et2O, 9:1) afforded the desired product as white solid, mp=41−42° C. (211 mg, 92%).

Workup

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

Sources & evidence

ORD record
ord-cb0da0974f1a4808815c61de6dc9e60c
Source dataset
uspto-grants-2013_06
Patent number
US08470982B2

Reaction notes

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