Sodium Carbonate → (+)-Solketal

HRID 1857060Notes

Reaction equation

HRID 1857060 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].C([O:15][CH2:16][C@H:17]1[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18]1)(=O)C1C=CC=CC=1>O>[CH3:22][C:19]1([CH3:23])[O:18][C@@H:17]([CH2:16][OH:15])[CH2:21][O:20]1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 12914085HCID 12914085, compound

Product 1

HCID 736057(+)-SolketalYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Then sodium carbonate (39.43 g, 0.372 mol) was added to a mixture of the crude (R)-4-benzoyloxymethyl-2,2-dimethyl-1,3-dioxolane (58.63 g, 0.248 mol) and water (130 ml resulting mixture was stirred for 8 hours at 100° C. After cooling the reaction mixture was extracted with methylene chloride. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and condensed in vacuo. The crude product was distilled to give 21.96 g of (S)-2,2-dimethyl-1,3-dioxolane-4-methanol (yield 67%, b.p. 65° C. at 3 mmHg, optical purity 97.3 % e.e., specific rotation [α]D20 +10.84°(c=1,MeOH)

Workup

  1. customresulting mixture
  2. temperatureAfter cooling the reaction mixture
  3. extractionwas extracted with methylene chloride
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate and condensed in vacuo
  6. distillationThe crude product was distilled

Sources & evidence

ORD record
ord-fc06a4ec61a84228aae7da07a3c95b35
Source dataset
uspto-grants-2000_11
Patent number
US06143908

Reaction notes

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