N-Hydroxyphthalimide → N-(4-octyloxybenzyloxy)phthalimide

HRID 974713

Reaction equation

HRID 974713 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH2:13]([O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][OH:27])=[CH:24][CH:23]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].O[N:31]1[C:35](=[O:36])[C:34]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:33]2[C:32]1=[O:41].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH2:13]([O:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:26][O:27][N:31]2[C:32](=[O:41])[C:33]3=[CH:40][CH:39]=[CH:38][CH:37]=[C:34]3[C:35]2=[O:36])=[CH:28][CH:29]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 144261p-Octyloxybenzyl alcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 19969096N-(4-octyloxybenzyloxy)phthalimideYield 83.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (18.4 g) was added dropwise to a suspension of 4-octyloxybenzyl alcohol (25 g), N-hydroxyphthalimide (17.15 g) and triphenylphosphine (27.74 g) in tetrahydrofuran (250 ml) under ice-cooling. The reaction mixture was stirred at room temperature for 2 hours, and evaporated in vacuo. The residue was purified by chromatography on silica gel to give N-(4-octyloxybenzyloxy)phthalimide (33.45 g) as crystals.

Workup

  1. temperaturecooling
  2. customevaporated in vacuo
  3. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e527255a53ed4f3889660a581d775414
Source dataset
uspto-grants-1997_03
Patent number
USH0001638

Linked notes

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