3-(1,1-DiMethylheptyl)phenol synthesis

6synthesis methods

Product Name:3-(1,1-DiMethylheptyl)phenol
CAS Number:70120-12-6
Molecular formula:C15H24O
Molecular Weight:220.35

Benzene, 1-(1,1-dimethylheptyl)-3-methoxy-

866398-21-2
0 suppliers
inquiry

70120-12-6
8 suppliers
$640.00/100mg

Yield:70120-12-6 94%

Reaction Conditions:

Stage #1: 1-(1,1-dimethylheptyl)-3-methoxybenzenewith boron tribromide in dichloromethane; for 2 h;
Stage #2: with water in dichloromethane;

Steps:

1 3-(1,1-Dimethylheptyl)-phenol (5)

Compound 4 (4.08 g, 17.74 mmol) and boron tribromide 1 M in DCM (35 mL, 35 mmol) were stirred for 2 h. The mixture was poured onto ice and water (400 mL), and the aqueous layer extracted with DCM (30 mL), dried (MgSO₄), and the solvent removed in vacuo. The residue was purified by flash chromatography, eluting with 20% EtOAc/cyclohexane to give the product as a brown oil (5) (3.66 g, 16.63 mmol, 94%):¹H NMR (CDCl₃) δ 7.19-7.14 (t, J=15, 1H), 6.92-6.89 (dd, J₁=1, J₂1, 1H), 4.83 (bs, 1H), 1.59-1.53 (m, 2H), 1.27-1.25 (d, J=6, 6H), 1.21-1.18 (d, 6H), 0.86-0.82 (t, J=12, 3H);¹³C NMR (CDCl₃) δ 155.20 (C, Ar), 152.11 (C, Ar), 129.06 (CH, Ar), 118.49 (CH, Ar), 113.12 (CH, Ar), 112.12 (CH, Ar), 44.60 (CH₂), 31.80 (CH₂), 30.04 (CH₂), 28.93 (CH₃), 24.68 (CH₂), 22.69 (CH₂), 14.11 (CH₃);MS (ESP^-) m/z 219.3 (M-1).