Hydrochloric Acid → 5-Chloromethylfurfural

HRID 262396

Reaction equation

HRID 262396 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 3037556(2R,3S,4S,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 the same three-necked flask as in Example 1 were added 5 g (0.028 mole) of a commercially available D-(+)-galactose and two kinds of surface active agent, i.e., 89.6 mg (0.00028 mole) of cetyltrimethylammonium chloride and 97.6 mg (0.00028 mole) of sodium laurylbenzenesulfonate. Then, 30 ml of toluene was added thereto and the mixture was stirred to make a suspension. Thereafter, about 6 ml of 35% aqueous hydrochloric acid was added dropwise from a dropping funnel over about 1 hour. A slight excess of hydrogen chloride was then slowly passed therethrough at 50° C. over 3 hours with stirring. After stirring was continued for a further 5 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 (theoretical yield 4.01 g) of 5-chloromethylfurfural as a crude product.

Workup

  1. stirringat 50° C. over 3 hours with stirring
  2. stirringAfter stirring
  3. filtrationfiltered through Celite
  4. washwhile being washed with toluene
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-37b182d5d2eb41d79c8e5f2a89c4a45a
Source dataset
uspto-grants-1979_05
Patent number
US04154744

Linked notes

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