Hydrochloric Acid → Sweetrex

HRID 1911986Notes

Reaction equation

HRID 1911986 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>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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 5984D-(-)-FructoseHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

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 the organic phase was collected. To the aqueous phase was added 10 mL MIBK and 50 μL aqueous solution of 0.5M aluminum chloride. 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 1.

Workup

  1. customsealed glass reactor tube at 140° C. for 1 hour
  2. temperatureThe reaction mixture was cooled
  3. customthe organic phase was collected
  4. additionTo the aqueous phase was added 10 mL MIBK and 50 μL aqueous solution of 0.5M aluminum chloride
  5. stirringThe mixture was stirred under a nitrogen atmosphere in a 25 mL
  6. customsealed glass reactor tube at 140° C. for two to four hours

Sources & evidence

ORD record
ord-29c0f4d910b248a8b64f1eb328c8ec07
Source dataset
uspto-grants-2013_12
Patent number
US08604225B2

Reaction notes

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