Methanol → 2-Methyl-2-phenyl-6-bromohexanol

HRID 873298Notes

Reaction equation

HRID 873298 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([CH3:18])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:7](OCC)=[O:8].[Li+].[BH4-].CO>C(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([CH3:18])([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:7][OH:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 11174430Ethyl 6-bromo-2-methyl-2-phenylhexanoate

Product 1

HCID 113002282-Methyl-2-phenyl-6-bromohexanolYield 84.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the procedure given for the synthesis of 206e, 205d (52.0 g, 166.0 mmol) was reacted with LiBH4 (5.4 g, 247.9 mmol) and methanol (8.2 g, 255.9 mmol) in CH2Cl2 (180 mL) to afford 206d (38.0 g, 84%) as an oil. 1H NMR (CDCl3): δ 7.5-7.1 (m, 5H), 3.60 (d, 1H, J=10.8), 3.53 (d, 1H, J=10.8), 3.34 (t, 2H, J=7.0), 1.90-1.78 (m, 3H), 1.62-1.26 (m, 3H), 1.35 (s, 3H), 1.14 (m, 1H). 13C NMR (CDCl3): δ 144.4, 128.4, 126.5, 126.1, 72.4, 43.2, 37.4, 33.5, 33.3, 22.5, 21.4.

Sources & evidence

ORD record
ord-6c838cec17ee43d3ab244e5884d7241d
Source dataset
uspto-grants-2015_03
Patent number
US08975300B2

Reaction notes

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