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

HRID 646828Notes

Reaction equation

HRID 646828 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([CH3:16])([C:9]1[CH:14]=[CH:13][C:12](C)=[CH:11][CH:10]=1)[CH2:7][OH:8].BrCCCCC(C)(C1C=CC=CC=1)C(OCC)=O.[Li+].[BH4-].CO>C(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([CH3:16])([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:7][OH:8]

Participants

6

Reactant 4

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 11174430Ethyl 6-bromo-2-methyl-2-phenylhexanoateHCID 111968926-Bromo-2-methyl-2-p-tolylhexan-1-ol

Product 1

HCID 113002282-Methyl-2-phenyl-6-bromohexanolYield 84%

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 (82 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-131a441c24b54ad4b28f6a8ab4fea913
Source dataset
uspto-grants-2010_04
Patent number
US07705177B2

Reaction notes

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