Hydrochloric Acid → 5-Chloromethylfurfural

HRID 262394

Reaction equation

HRID 262394 reaction equation
C(O)[C@H]1O[C@H](O[C@:9]2([CH2:18]O)[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11](O)[C@@H:10]2O)[C@H](O)[C@@H](O)[C@@H]1O.C(OS(C1C=CC=CC=1)(=O)=O)CCCCCCCCCCC.[Na].O.[ClH:48]>[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.C1(C)C=CC=CC=1>[Cl:48][CH2:18][C:9]1[O:13][C:12]([CH:14]=[O:15])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 5988SucroseHCID 57371080Sodium dodecylbenzene sulphonate

Product 1

HCID 741915-Chloromethylfurfural

Reagents, catalysts & solvents 2

HCID 8154Hexadecyltrimethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

To a three-necked flask equipped with a condenser and a stirrer were added 5 g (0.014 mole) of a commercially available D-(+)-saccharose and two kinds of surface active agent, i.e., 47.1 mg (0.00014 mole) of cetyltrimethylammonium chloride and 51.3 mg (0.00014 mole) of sodium laurylbenzenesulfonate. 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 about 30 minutes with thorough stirring. After the reaction was continued at room temperature for a further 3 hours, the upper toluene layer was separated from the lower aqueous layer. Thirty milli-liters of toluene and the above two surface active agents of the same amounts as above were then freshly added to the aqueous layer. After the reaction was carried out at room temperature for 3 hours, the upper toluene layer was again separated. This toluene extraction operation was repeated three times in total. All the toluene layers were combined and filtered through Celite. The filtrate was neutralized with an aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate and concentrated. Thus, about 2.6 g of 5 -chloromethylfurfural was obtained as a crude product.

Workup

  1. customTo a three-necked flask equipped with a condenser and a stirrer
  2. customthe upper toluene layer was separated from the lower aqueous layer
  3. additionThirty milli-liters of toluene and the above two surface active agents of the same amounts as above were then freshly added to the aqueous layer
  4. waitAfter the reaction was carried out at room temperature for 3 hours
  5. customthe upper toluene layer was again separated
  6. extractionThis toluene extraction operation
  7. filtrationfiltered through Celite
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-65db85bb71f34eae8caae5b5385e7a9a
Source dataset
uspto-grants-1979_05
Patent number
US04154744

Linked notes

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