Furfuryl Alcohol → N-(2-Furylmethoxy)phthalimide

HRID 1283384Notes

Reaction equation

HRID 1283384 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-ebffe85cb5bf46b5aabde948c7b7f344
Source dataset
uspto-grants-1976_08
Patent number
US03975376

Reaction notes

Loading…