Hydrochloric Acid → 5-Chloromethylfurfural

HRID 262402Notes

Reaction equation

HRID 262402 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].O.[ClH:37]>[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.C(Cl)(Cl)(Cl)Cl>[Cl:37][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 962WaterHCID 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 5943Carbon TetrachlorideSolvent

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 carbon tetrachloride 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 which seemed to gel slightly was filtered through Celite while being washed with small amounts of water and carbon tetrachloride. The lower carbon tetrachloride layer was neutralized, dried and concentrated to obtain about 1.5 g of 5-chloromethylfurfural.

Workup

  1. stirringStirring
  2. filtrationslightly was filtered through Celite
  3. washwhile being washed with small amounts of water and carbon tetrachloride
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6f2f3b2043874e68bd8b083f1793209a
Source dataset
uspto-grants-1979_05
Patent number
US04154744

Reaction notes

Loading…