Methanol → 7-Bromo-2,2-dimethylheptan-1-ol

HRID 646829Notes

Reaction equation

HRID 646829 reaction equation
BrCCCCC(C)(C1C=CC(C)=CC=1)CO.[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([CH3:30])([CH3:29])[C:24](OCC)=[O:25].[Li+].[BH4-].CO>C(Cl)Cl>[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([CH3:30])([CH3:29])[CH2:24][OH:25]

Participants

6

Reactant 4

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 111968926-Bromo-2-methyl-2-p-tolylhexan-1-olHCID 11265571Ethyl 7-bromo-2,2-dimethylheptanoate

Product 1

HCID 113106207-Bromo-2,2-dimethylheptan-1-olYield 101.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the method for the synthesis of 206e, 205g (43.0 g, 0.16 mol) was treated with LiBH4 (5.55 g, 0.25 mol) and methanol (7.75 g, 0.24 mol) in CH2Cl2 (200 mL) to give 206g (36.2 g, 98%) as a colorless, viscous oil. 1H NMR (CDCl3): δ 3.41 (t, 2H, J=6.9), 3.30 (br. s, 2H), 1.90-1.84 (m, 3H), 1.42-1.22 (m, 6H), 0.86 (s, 6H). 13C NMR (CDCl3): δ 71.9, 38.6, 35.1, 34.1, 32.9, 29.2, 24.0, 23.2. HRMS (LSIMS, nba): Calcd for C9H18Br (MH+—H2O): 205.0592, found: 205.0563.

Sources & evidence

ORD record
ord-198a4479282442e8b8b19a6c33d0e5e4
Source dataset
uspto-grants-2010_04
Patent number
US07705177B2

Reaction notes

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