1,2-Epoxy-3-methylbutane → 2-(2-(3-(2-Hydroxy-3-methylbutoxy)phenoxy)ethyl)isoindoline-1,3-dione

HRID 74407Notes

Reaction equation

HRID 74407 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[O:5][CH2:6][CH2:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18].[O:22]1[CH:24]([CH:25]([CH3:27])[CH3:26])[CH2:23]1>>[OH:22][CH:24]([CH:25]([CH3:27])[CH3:26])[CH2:23][O:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[O:5][CH2:6][CH2:7][N:8]1[C:9](=[O:18])[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]1=[O:17]

Participants

3

Reactant 2

HCID 1026181,2-Epoxy-3-methylbutaneHCID 580275342-[2-(3-Hydroxy-phenoxy)-ethyl]-isoindole-1,3-dione

Product 1

HCID 673168722-(2-(3-(2-Hydroxy-3-methylbutoxy)phenoxy)ethyl)isoindoline-1,3-dione

Procedure

Alkylation reaction of phenol 24 with 1,2-epoxy-3-methylbutane gave 2-(2-(3-(2-hydroxy-3-methylbutoxy)phenoxy)ethyl)isoindoline-1,3-dione as yellow oil. Yield (1.0 g, 76%): 1H NMR (400 MHz, CDCl3) δ 8.01-8.03 (m, 1H), 7.47-7.55 (m, 3H), 7.13-7.17 (m, 1H), 6.49-6.54 (m, 3H), 4.12 (t, J=5.6 Hz, 2H), 3.98-4.02 (m, 1H), 3.82-3.88 (m, 3H), 3.68-3.73 (m, 1H), 1.82-1.88 (m, 1H), 1.01 (d, J=6.8 Hz, 3H), 0.91 (d, J=6.8 Hz, 3H).

Sources & evidence

ORD record
ord-88ed731cbba345a8a3c9bd91fc2ce4d9
Source dataset
uspto-grants-2014_09
Patent number
US08829244B2

Reaction notes

Loading…