Hydrochloric Acid → 5-Chloromethylfurfural

HRID 262401Notes

Reaction equation

HRID 262401 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11]O)[OH:10])O)O)O.C(OS(C1C=CC=CC=1)(=O)=O)CCCCCCCCCCC.[Na].C1(C)C=CC=CC=1.[ClH:43]>[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.O>[Cl:43][CH2:11][C:9]1[O:10][C:3]([CH:2]=[O:1])=[CH:5][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 57371080Sodium dodecylbenzene sulphonate

Product 1

HCID 741915-Chloromethylfurfural

Reagents, catalysts & solvents 2

HCID 8154Hexadecyltrimethylammonium chlorideCatalystHCID 962WaterSolvent2×

Procedure

To the same three-necked flask were added 5 g of a commercially available D-glucose and two kinds of surface active agent, i.e., 97.6 mg of sodium laurylbenzenesulfonate and 89.6 mg of cetyltrimethylammonium chloride. Then, 5 ml of water and 30 ml of toluene were added thereto and the mixture was stirred. Thereafter, a molar excess of hydrogen chloride was passed through the mixture at room temperature for 25 minutes. Stirring was continued at 50° C. for a further 7 hours. The reaction solution was diluted with a little water and filtered through Celite while being washed with toluene. The toluene layer was treated in the same manner to obtain about 1.7 g of 5-chloromethylfurfural.

Workup

  1. stirringStirring
  2. filtrationfiltered through Celite
  3. washwhile being washed with toluene
  4. additionThe toluene layer was treated in the same manner

Sources & evidence

ORD record
ord-9c9d8a4ec7104e3c9b525acc8d9ac687
Source dataset
uspto-grants-1979_05
Patent number
US04154744

Reaction notes

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