Water → L-ASCORBIC ACID 2-MONOPHOSPHATE TRI-CYCLOHEXYLAMMONIUM SALT

HRID 1195248Notes

Reaction equation

HRID 1195248 reaction equation
CC1(C)[O:6][C@H:5]([C@H:7]2[O:12][C:10](=[O:11])[C:9]([OH:13])=[C:8]2[OH:14])[CH2:4][O:3]1.[OH2:16].[P:17](Cl)(Cl)(Cl)=[O:18].[OH-:22].[Na+]>N1C=CC=CC=1>[P:17]([O:13][C:9]1[C:10]([O:12][C@H:7]([C@H:5]([CH2:4][OH:3])[OH:6])[C:8]=1[OH:14])=[O:11])([OH:18])([OH:22])=[O:16]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 54691418(+)-5,6-O-Isopropylidene-L-ascorbic acid2×

Product 1

HCID 54679073L-ASCORBIC ACID 2-MONOPHOSPHATE TRI-CYCLOHEXYLAMMONIUM SALTYield 86%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

U.S. Pat. No. 4,179,445 discloses another improved method in which 5,6-isopropylidene-L-ascorbic acid, a phosphorus oxyhalide of general formula POX3 (wherein X is a halogen atom) and a specific solvent (a mixed solvent composed of water and a tertiary amine) are mixed with each other and the mixture is kept at pH 13 or higher to react. More particularly, 5,6-isopropylidene-L-ascorbic acid is dissolved in a mixed solvent composed of water and pyridine, and phosphorus oxychloride is added dropwise to the mixture at -10° C. to +10° C. In this case, an aqueous solution of 10M sodium hydroxide is added dropwise to the mixture while stirring in order to carry out the reaction in a higher pH range (e.g., about pH 13). After completion of the reaction, the reaction mixture is cooled to room temperature, treated with a strongly acidic cation exchange resin (H+ -form) for desalting and purification, followed by neutralization with magnesium oxide and removal of the solvent by distillation and dropwise addition of ethanol to the residue to give white powder of magnesium salt of L-ascorbic acid 2-phosphate, which is collected by filtration (yield: 86%).

Workup

  1. customhigher to react
  2. additionis added dropwise to the mixture at -10° C. to +10° C
  3. customthe reaction in a higher pH range (e.g., about pH 13)
  4. customAfter completion of the reaction
  5. additiontreated with a strongly acidic cation exchange resin (H+ -form)
  6. custompurification
  7. customfollowed by neutralization with magnesium oxide and removal of the solvent by distillation and dropwise addition of ethanol to the residue

Sources & evidence

ORD record
ord-068f9bc5ff1c45ab83ebbbc69092d056
Source dataset
uspto-grants-1992_05
Patent number
US05110951

Reaction notes

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