Furfuryl Alcohol → N-(2-Furylmethoxy)phthalimide

HRID 1679199Notes

Reaction equation

HRID 1679199 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][C:21]1[O:22][CH:23]=[CH:24][CH:25]=1.C(O)C1OC=CC=1>O.CS(C)=O>[CH2:20]([O:1][N:2]1[C:3](=[O:12])[C:4]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]2[C:6]1=[O:7])[C:21]1[O:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 7361Furfuryl AlcoholHCID 10665N-HydroxyphthalimideHCID 11430Potassium CarbonateHCID 2195202-(Chloromethyl)furan

Product 1

HCID 19975015N-(2-Furylmethoxy)phthalimideYield 70%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a stirred mixture of N-hydroxyphthalimide (41 g.), anhydrous potassium carbonate (26.4 g.) and dry dimethyl sulphoxide (400 ml.) was added 2-chloromethylfuran (freshly prepared, but undistilled, from 46.2 g. furfuryl alcohol according to the method of W. R. Kirner JACS, 1928, 50, 1955). The mixture was stirred for 18 hr., then poured into water (1.5 l). The precipitated solid was filtered off, washed well with water, and recrystallised from ethanol to give N-furfuryloxyphthalimide (42.8 g., 70%), m.p. 145.3°-146.2° τ values (DMSO-d6) are 4.80 (CH2), 2.22, 3.30, 3.50 (furyl protons) 2.08 (phthalimide protons).

Workup

  1. customfreshly prepared
  2. filtrationThe precipitated solid was filtered off
  3. washwashed well with water
  4. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-9e4b26403f34484bb7bfca3d299f464e
Source dataset
uspto-grants-1978_03
Patent number
US04079178

Reaction notes

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