Hydrochloric Acid → 5-Chloromethylfurfural

HRID 262400

Reaction equation

HRID 262400 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 Acid2×HCID 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 962WaterSolvent

Procedure

To a three-necked flask equipped with a condenser and a stirrer were added 5 g (0.028 mole) of a commercially available D-glucose and two kinds of surface active agent, i.e., 97.6 mg (0.00028 mole) of sodium laurylbenzenesulfonate and 89.6 mg (0.00028 mole) of cetyltrimethylammonium chloride. Then, 30 ml of toluene was added thereto and the mixture was stirred to make a suspension. Thereafter, about 6 ml of 35% hydrochloric acid was slowly dropwise added from a dropping funnel over 1 hour with stirring. A slight excess of hydrogen chloride was then slowly passed therethrough at 45° C. over 3 hours with stirring. After stirring was continued for a further 4 hours, the reaction solution was diluted with a little water and filtered through Celite while being washed with toluene. The toluene layer was neutralized, dried and concentrated to obtain about 1.9 g of 5-chloromethylfurfural.

Workup

  1. customTo a three-necked flask equipped with a condenser and a stirrer
  2. stirringwith stirring
  3. stirringat 45° C. over 3 hours with stirring
  4. stirringAfter stirring
  5. filtrationfiltered through Celite
  6. washwhile being washed with toluene
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-06ec1e8c1cd547ffad15da46e304360d
Source dataset
uspto-grants-1979_05
Patent number
US04154744

Linked notes

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