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

Participants

Role	Name	HCID	Charge
Reactant	Methanol	HCID 887	—
Reactant	Lithium borohydride	HCID 4148881	—
Reactant	Ethyl 6-bromo-2-methyl-2-phenylhexanoate	HCID 11174430	—
Reactant	6-Bromo-2-methyl-2-p-tolylhexan-1-ol	HCID 11196892	—
Solvent	Dichloromethane	HCID 6344	—
Product	2-Methyl-2-phenyl-6-bromohexanol	HCID 11300228	84%

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08084498B2
Source dataset	uspto-grants-2011_12
ORD ID	ord-8b40b5e0263640148b7ac160f7a16a4e
Source note	uspto-grants-2011_12