Dichloromethane → 2-Benzyl-4-ethoxy-6-allyl-7-hydroxysaccharin

HRID 266474Notes

Reaction equation

HRID 266474 reaction equation
[CH2:1]([N:8]1[C:18](=[O:19])[C:17]2[C:12](=[C:13]([O:23]CC=C)[CH:14]=[CH:15][C:16]=2[O:20][CH2:21][CH3:22])[S:9]1(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COCCOCCO[CH2:35][CH2:36]OC.Cl[CH2:40]Cl>>[CH2:1]([N:8]1[C:18](=[O:19])[C:17]2[C:12](=[C:13]([OH:23])[C:14]([CH2:40][CH:35]=[CH2:36])=[CH:15][C:16]=2[O:20][CH2:21][CH3:22])[S:9]1(=[O:10])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 8189TriglymeHCID 700509212-Benzyl-4-ethoxy-7-allyloxysaccharin

Product 1

HCID 700530822-Benzyl-4-ethoxy-6-allyl-7-hydroxysaccharinYield 36%

Conditions

Temperature
200 °C

Procedure

A mixture of 2-benzyl-4-ethoxy-7-allyloxysaccharin (0.25 g) and triglyme was heated at 200° C. for 20 minutes, examined for extent of reaction by thin layer chromatography, heated at 200° C. for 20 minutes more, stirred overnight and poured into ice-water. The resulting tacky, brown solid was dissolved in dichloromethane. The dichloromethane solution was washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and stripped of dichloromethane. Column chromatography of the residue (0.29 g) on silica using dichloromethane and dichloromethane-acetone (up to 99:1) as eluants afforded 2-benzyl-4-ethoxy-6-allyl-7-hydroxysaccharin (90 mg, 36% yield) whose mass spectrogram showed a molecular ion at mass 373.

Workup

  1. customexamined for extent of reaction by thin layer chromatography
  2. temperatureheated at 200° C. for 20 minutes more
  3. washThe dichloromethane solution was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-7fd7ed211adf49958b19d8715b7eccaf
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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