1-Chloro-2-methylbutane → 2-(2-Methylbutylthio)phenol
Reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].Cl[CH2:10][CH:11]([CH3:14])[CH2:12][CH3:13]>>[CH3:10][CH:11]([CH2:12][CH3:13])[CH2:14][S:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8]Participants
3
Procedure
This compound was prepared in 57% yield from 2-mercaptophenol and 1-chloro-2-methylbutane according to the procedure for 1p in Example VIII. 1H NMR (CDCl3): δ 0.86 (t, J=4.85 Hz, 3H), 1.00 (d, J=6.60 Hz, 3H), 1.18-1.27 (m, 1H), 1.46-1.58 (m, 2H), 2.55 (dd, J=7.15, J=12.35, 1H), 2.70 (dd, J=5.75, 12.65, 1H), 6.75 (d, J=1.1 Hz), 6.86 (dt, J=1.1 Hz, J=4.93 Hz, 1H), 6.98 (dd, J=1.4 Hz, J=8.25 Hz, 1H), 7.24 (dt, J=1.65 Hz, J=7.40 Hz, 1H, 7.45 (dd, J=1.65 Hz, J=7.70 Hz, 1H); 13C NMR (CDCl3): δ 11.26, 18.74, 28.56, 34.80, 44.36, 114.77, 119.98, 120.81, 130.89, 135.80, 156.80; HRMS (FAB): 196.09219 calcd for C11H16OS [M]+. found 196.09293 (3.6 ppm, 0.7 mmu).
Sources & evidence
- ORD record
- ord-a74f210ae2df454dacde7c8a1b420c90
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618162B2
Reaction notes
Loading…