Furfuryl Alcohol → N-(2-Furylmethoxy)phthalimide

HRID 328446

Reaction equation

HRID 328446 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>[O:22]1[CH:23]=[CH:24][CH:25]=[C:21]1[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]

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-(fur-2-ylmethoxy)phthalimide (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-fff37ae685fb4a99b5bf14a1e6a93874
Source dataset
uspto-grants-1977_04
Patent number
US04017515

Linked notes

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