Methanol → 5-Bromo-2,2-dimethylpentan-1-ol

HRID 661172Notes

Reaction equation

HRID 661172 reaction equation
BrCCCCC(C)(C1C=CC(C)=CC=1)CO.[Br:17][CH2:18][CH2:19][CH2:20][C:21]([CH3:28])([CH3:27])[C:22](OCC)=[O:23].[Li+].[BH4-].CO>C(Cl)Cl>[Br:17][CH2:18][CH2:19][CH2:20][C:21]([CH3:28])([CH3:27])[CH2:22][OH:23]

Participants

6

Reactant 4

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 10681333Ethyl 5-bromo-2,2-dimethylpentanoateHCID 111968926-Bromo-2-methyl-2-p-tolylhexan-1-ol

Product 1

HCID 111831775-Bromo-2,2-dimethylpentan-1-olYield 108.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the procedure given for the synthesis of 206e, 205a (94.0 g, 0.37 mol) was reduced with LiBH4 (12.97 g, 0.60 mol) and methanol (19.04 g, 0.60 mol) in CH2Cl2 (400 mL) to give 206a (78.0 g, 100%) as an oil. 1H NMR (DMSO-d6): δ 4.42 (s, 1H), 3.45 (t, 2H, J=6.6), 3.08 (s, 2H), 1.84-1.69 (m, 2H), 1.27 (t, 2H, J=8.3), 0.78 (s, 6H). 13C NMR (DMSO-d6): δ 69.7, 36.9, 35.7, 34.5, 27.4, 24.0.

Sources & evidence

ORD record
ord-be16a387dfde4ba7a7e5354d9dfd4313
Source dataset
uspto-grants-2011_12
Patent number
US08084498B2

Reaction notes

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