Hydrochloric Acid → Sweetrex

HRID 1911987Notes

Reaction equation

HRID 1911987 reaction equation
[Cl-].[Na+].[O:3]=[CH:4][C@@H:5]([C@H:7]([C@@H:9]([C@@H:11]([CH2:13][OH:14])[OH:12])[OH:10])[OH:8])[OH:6].[OH:15][CH2:16][C:17]([C@H:19]([C@@H:21]([C@@H:23]([CH2:25][OH:26])[OH:24])[OH:22])[OH:20])=[O:18].Cl.[Cl-].[Al+3].[Cl-].[Cl-]>CC(CC(C)=O)C>[OH:3][CH2:4][C:5]([C@H:7]([C@@H:9]([C@@H:11]([CH2:13][OH:14])[OH:12])[OH:10])[OH:8])=[O:6].[O:15]=[CH:16][C@@H:17]([C@H:19]([C@@H:21]([C@@H:23]([CH2:25][OH:26])[OH:24])[OH:22])[OH:20])[OH:18]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 5984D-(-)-FructoseHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3082460Sweetrex

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

2.5 mL of an aqueous solution of 245 g/L sodium chloride, 171 g/L glucose, 123 g/L fructose and 0.36 g/L hydrogen chloride was added 10 mL MIBK and stirred under a nitrogen atmosphere in a 25 mL sealed glass reactor tube at 140° C. for 1 hour. The reaction mixture was cooled and 50 μL aqueous solution of 0.5M aluminum chloride was added. The mixture was stirred under a nitrogen atmosphere in a 25 mL sealed glass reactor tube at 140° C. for two to four hours. The aqueous and organic phases were analyzed by HPLC. The results are given in table 2.

Workup

  1. customsealed glass reactor tube at 140° C. for 1 hour
  2. temperatureThe reaction mixture was cooled
  3. stirringThe mixture was stirred under a nitrogen atmosphere in a 25 mL
  4. customsealed glass reactor tube at 140° C. for two to four hours

Sources & evidence

ORD record
ord-e8caca76d7cc45babd4fff78cbafa4d0
Source dataset
uspto-grants-2013_12
Patent number
US08604225B2

Reaction notes

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