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

HRID 661175Notes

Reaction equation

HRID 661175 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 (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-8b40b5e0263640148b7ac160f7a16a4e
Source dataset
uspto-grants-2011_12
Patent number
US08084498B2

Reaction notes

Loading…