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

HRID 239082Notes

Reaction equation

HRID 239082 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, 5 H), 3.60 (d, 1 H, J=10.8), 3.53 (d, 1 H, J=10.8), 3.34 (t, 2 H, J=7.0), 1.90-1.78 (m, 3 H), 1.62-1.26 (m, 3 H), 1.35 (s, 3 H), 1.14 (m, 1 H). 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-ddeee37e076e4c10b2df2e93e226ee67
Source dataset
uspto-grants-2014_02
Patent number
US08642653B2

Reaction notes

Loading…