1-Octanol → 1-(4-(Octyloxy)-3-(trifluoromethyl)phenyl)ethanone

HRID 2357088Notes

Reaction equation

HRID 2357088 reaction equation
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].F[C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][C:12]=1[C:20]([F:23])([F:22])[F:21].CC(C)([O-])C.[K+]>O1CCCC1>[CH2:1]([O:9][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][C:12]=1[C:20]([F:21])([F:22])[F:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 9571-OctanolHCID 6056784'-Fluoro-3'-(trifluoromethyl)acetophenoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 593844461-(4-(Octyloxy)-3-(trifluoromethyl)phenyl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-octanol (2 mL), 1-[4-fluoro-3-(trifluoromethyl)phenyl]ethanone (2.62 g), potassium tert-butoxide (14 mL, 1.0M) and tetrahydrofuran (30 mL) were heated at 65° C. for 3 hrs to produce the title product as a brownish oil (4.00 g). The product was purified by silica gel column chromatography using the Combi-Flash system (Hex:EtOAc) as white solid in 60% (1.20 g). TLC (1:5 EtOAc:Hex), Rf=0.4; 1H NMR (400 MHz, CDCl3) δ 8.18 (d, 1H, J=2.0 Hz), 8.10 (dd, 1H, J=8.8 Hz, J=2.3 Hz), 7.02 (d, 1H, J=8.8 Hz), 4.12 (t, 2H, J=6.4 Hz), 2.58 (m, 3H), 1.80-1.89 (m, 2H), 1.42-1.54 (m, 2H), 1.22-1.40 (m, 8H), 0.89 (t, 3H, J=6.7 Hz).

Sources & evidence

ORD record
ord-b61b1ace2b0447b2b1b9d08c06f61fd6
Source dataset
uspto-grants-2010_07
Patent number
US07759370B2

Reaction notes

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