Methanol → HCID 86593944, compound

HRID 2181735Notes

Reaction equation

HRID 2181735 reaction equation
[C:1]([Cl:4])(=[O:3])C.O=C([O-])[C@@H:7]([C@H:9]([C@H:11]([C@@H:13]([C:15]([O-:17])=[O:16])[OH:14])[OH:12])[OH:10])[OH:8].[C:19]1([CH2:27][NH3+:28])[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][NH3+:26])[CH:20]=1.[CH3:29][OH:30]>>[O:30]=[C:29]([O:3][CH3:1])[C@@H:7]([C@H:9]([C@H:11]([C@@H:13]([C:15]([O:17][CH3:19])=[O:16])[OH:14])[OH:12])[OH:10])[OH:8].[Cl-:4].[Cl-:4].[C:19]1([CH2:27][NH3+:28])[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][NH3+:26])[CH:20]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 6367Acetyl chlorideHCID 86593943HCID 86593943, compound

Product 1

HCID 86593944HCID 86593944, compoundYield 88.94%

Procedure

Acetyl chloride (2 mL) was added drop-wise over a period of 5 min to methanol (25 mL) maintained in an ice-bath. m-Xylylenediammonium galactarate (14, 1.008 g, 2.910 mmol) was then to the solution and the reaction was allowed to reflux for 4 h. Within 1 h complete dissolution had occurred. The solvent was removed under reduced pressure and the remaining white powder dried under vacuum at room temperature for 16 h to give white solid 1:1 dimethyl galactarate/m-xylylenediammonium dichloride (20, 1.158 g, 2.588 mmol, 88.94%).

Workup

  1. temperaturemaintained in an ice-bath
  2. temperatureto reflux for 4 h
  3. dissolutionWithin 1 h complete dissolution
  4. customThe solvent was removed under reduced pressure
  5. customthe remaining white powder dried under vacuum at room temperature for 16 h

Sources & evidence

ORD record
ord-fc03f5d575b845f49b770f5d1a2eb69f
Source dataset
uspto-grants-2005_05
Patent number
US06894135B2

Reaction notes

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