Methanol → 2,2-Dimethoxypropane-1,3-diol

HRID 1443323Notes

Reaction equation

HRID 1443323 reaction equation
CO[CH:3]([O:6][CH3:7])[O:4][CH3:5].C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:19]([O-:22])([O-])=O.[Na+].[Na+].[CH3:25][OH:26]>>[CH3:7][O:6][C:3]([O:4][CH3:5])([CH2:19][OH:22])[CH2:25][OH:26]

Participants

5

Reactant 4

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 10340Sodium Carbonate

Product 1

HCID 111263102,2-Dimethoxypropane-1,3-diolYield 47%

Procedure

2,2-dimethoxy-propane-1,3-diol (III) was synthesized according to the method of Ferroni, E. L., et al., J. Org. Chem., 64, 4943-4945 (1999). DHA dimer (25 g, 0.139 mole), trimethylorthoformate (30.4 ml, 0.278 mole) and p-toluenesulfonic acid (100 mg) were combined in 300 mL of methanol and stirred for 12 h. At this time 300 mg of Na2CO3 were added and the reaction mixture was stirred for an additional 12 h, after which the mixture was filtered and solvent was removed in vacuo. The resulting solid was recrystallized from ethyl ether to give 17.5 g of III (47%). 1H NMR (D2O) δ 3.58 (s; 4H), 3.24 (s; 6H). Anal. Calc.: C, 44.12; H, 8.82. Found: C, 44.50; H, 8.78.

Workup

  1. custom2,2-dimethoxy-propane-1,3-diol (III) was synthesized
  2. stirringthe reaction mixture was stirred for an additional 12 h
  3. filtrationafter which the mixture was filtered
  4. customsolvent was removed in vacuo
  5. customThe resulting solid was recrystallized from ethyl ether

Sources & evidence

ORD record
ord-1baf0c1b0999453b971f35d488c75d91
Source dataset
uspto-grants-2010_02
Patent number
US07659420B2

Reaction notes

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