Oxirane, 2-propyl- → 2-(2-(3-(2-Hydroxypentyloxy)phenoxy)ethyl)isoindoline-1,3-dione

HRID 875584Notes

Reaction equation

HRID 875584 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]([CH2:25][CH2:26][CH3:27])[CH2:23]1>>[OH:22][CH:24]([CH2:25][CH2:26][CH3:27])[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 13853Oxirane, 2-propyl-HCID 580275342-[2-(3-Hydroxy-phenoxy)-ethyl]-isoindole-1,3-dione

Product 1

HCID 673170242-(2-(3-(2-Hydroxypentyloxy)phenoxy)ethyl)isoindoline-1,3-dione

Procedure

Alkylation reaction of phenol 24 with 1,2-epoxypentane gave 2-(2-(3-(2-hydroxypentyloxy)phenoxy)ethyl)isoindoline-1,3-dione as yellow oil. Yield (1.1 g, 84%): 1H NMR (400 MHz, CDCl3) δ 7.98 (d, J=6.8 Hz, 1H), 7.44-7.56 (m, 2H), 7.12-7.16 (m, 1H), 6.68-6.73 (m, 1H), 6.46-6.52 (m, 3H), 4.10 (t, J=5.2 Hz, 2H), 3.90-4.0 (m, 2H), 3.77-3.82 (m, 3H), 1.32-1.56 (m, 4H), 0.94 (t, J=6.8 Hz, 3H).

Sources & evidence

ORD record
ord-c2d0abf6e89a44d18cf9bc67475ff69a
Source dataset
uspto-grants-2015_03
Patent number
US08981153B2

Reaction notes

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