Methane → Isopropylideneglycerol

HRID 2306125Notes

Reaction equation

HRID 2306125 reaction equation
[OH:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4].[CH3:7][C:8]1C=CC(S(O)(=O)=O)=C[CH:13]=1.C>CC(C)=O>[C:8](=[C:2]([CH:3]([CH2:5][OH:6])[OH:4])[OH:1])([CH3:13])[CH3:7]

Participants

5

Reactant 3

HCID 297MethaneHCID 753GlycerolHCID 6101p-Toluenesulfonic acid

Product 1

HCID 9920395Isopropylideneglycerol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Freshly distilled glycerol (10 g, 0. 11 mole) was shaken until dissolved with 65 mL of dry acetone containing 1 g of TsOH. After 24 hr. the solution was neutralized first with PbCO3 and afterwards with Ag2CO3, warmed with charcoal, and shaken with a large excess of CaCI2 overnight. The supernatant liquid was then filtered. The solvent was removed by rotary evaporation, and the product fractionated under diminished pressure, giving 9.5 g of the main fraction (b.p. 105-106° C./25 mm) Y=65.4%. NMR: 1H: δ (ppm) 4.14-4.16 (m,1H, CH), 3.65-4.0 (qxd, 2H, CH2),3.57 (m, 2H, CH2OH), 2.05 (sb. 1H,OH), 1.40, 1.33 (CH3); 13C: δ (ppm) 109.4 (COO), 76.1 (CH), 65.7 (CH2O), 62.8 (CH2OH), 26.6, 25.2 (CH3).

Workup

  1. filtrationThe supernatant liquid was then filtered
  2. customThe solvent was removed by rotary evaporation
  3. customgiving 9.5 g of the main fraction (b.p. 105-106° C./25 mm) Y=65.4%

Sources & evidence

ORD record
ord-acf0db553b254685a938a4370cd3bc50
Source dataset
uspto-grants-2002_08
Patent number
US06441214B1

Reaction notes

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