Mannitol → HCID 19915559, compound

HRID 1089651Notes

Reaction equation

HRID 1089651 reaction equation
[CH2:1]([OH:12])[C@H:2]([C@H:4]([C@@H:6]([C@@H:8]([CH2:10][OH:11])[OH:9])[OH:7])[OH:5])[OH:3].[CH:13]([O:15][CH2:16][CH3:17])=[CH2:14]>Cl.CN1C(=O)CCC1>[CH2:13]([O:15][CH:16]([O:12][CH2:1][CH:2]([O:3][CH:13]([O:15][CH2:16][CH3:17])[CH3:14])[CH:4]([O:5][CH:13]([O:15][CH2:16][CH3:17])[CH3:14])[CH:6]([O:7][CH:13]([O:15][CH2:16][CH3:17])[CH3:14])[CH:8]([O:9][CH:13]([O:15][CH2:16][CH3:17])[CH3:14])[CH2:10][O:11][CH:13]([O:15][CH2:16][CH3:17])[CH3:14])[CH3:17])[CH3:14]

Participants

5

Reactant 2

HCID 6251MannitolHCID 8023Ethyl vinyl ether

Product 1

HCID 19915559HCID 19915559, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Into a 250 ml. flask, equi ped with static nitrogen head and magnetic stirrer, was charged 18.6 g. of mannitol, 100 ml. of N-methyl pyrrolidinone and 64.8 g. of ethyl vinyl ether. There was then added 10 drops of concentrated HCl and the mixture stirred at between 22° and 28° for 4.5 hours and allowed to stand overnight. The next day an infrared spectrum of an appropriately worked up sample showed the virtual absence of hydroxyl absorption and strong ether C--O--C bands. The reaction mixture was poured, with stirring, into 750 ml. of water containing excess NaOH and extracted twice with 150 ml. portions of hexane. Each extract was washed consecutively with two 750 ml. portions of water. The compbined oganic phases were dried over solid sodium carbonate-sodium sulfate and vacuum evaporated at about 10 mm. Hg to give 59 g. of crude oil. Distillation was performed on a short path micro still under the following conditions:

Workup

  1. customflask, equi ped with static nitrogen head and magnetic stirrer
  2. additionwas charged 18.6 g
  3. waitto stand overnight
  4. customthe virtual absence of hydroxyl absorption and strong ether C--O--C bands
  5. additionThe reaction mixture was poured
  6. stirringwith stirring, into 750 ml
  7. extractionof water containing excess NaOH and extracted twice with 150 ml
  8. washEach extract was washed consecutively with two 750 ml
  9. dry with materialThe compbined oganic phases were dried over solid sodium carbonate-sodium sulfate and vacuum
  10. customevaporated at about 10 mm. Hg
  11. customto give 59 g
  12. distillationDistillation

Sources & evidence

ORD record
ord-7c6561129f8745c0b48ed8fc84dd3095
Source dataset
uspto-grants-1992_01
Patent number
US05079023

Reaction notes

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