Phthalic Anhydride → Phthalimide

HRID 1080845Notes

Reaction equation

HRID 1080845 reaction equation
[C:1]1(=O)[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[NH2:12]CCCCCCO>C1(C)C=CC=CC=1>[C:1]1(=[O:6])[NH:12][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 199606-Amino-1-hexanol

Product 1

HCID 6809Phthalimide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of phthalic anhydride (32.0 g, 0.21 mol) and 6-aminohexanol (25.0 g, 0.21 mol) in 180 mL dry toluene was heated to reflux for 3 hrs. When the intermediate phthalimide was formed, PBr3 (18.2 mL, 0.58 mol in 20 mL toluene) was added dropwise and the reaction was stirred at 100° C. for 1.5 hrs. The reaction mixture was filtered thru a microfiber filter and the filtrate was concentrated in vacuo to give the crude product which then crystallized from toluene to give 6-phthalimido-1-bromohexane. (86% yield).

Workup

  1. temperatureto reflux for 3 hrs

Sources & evidence

ORD record
ord-9e519693d910479a80a12849221278ba
Source dataset
uspto-grants-1996_12
Patent number
US05583146

Reaction notes

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