Sodium Carbonate → (+)-Solketal

HRID 1857056Notes

Reaction equation

HRID 1857056 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].C([O:15][CH2:16][CH: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 571151(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl benzoate

Product 1

HCID 736057(+)-SolketalYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Then sodium carbonate (24.80 g, 0.234 mol) was added to a mixture of the crude 4-benzoyloxymethyl-2,2-dimethyl-1,3-dioxolane (36.95 g, 0.156 mol) and water (80 ml) and 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 15.67 g of (S)-2,2-dimethyl-1,3-dioxolane-4-methanol (yield 76%, b.p. 72° C. at 8 mmHg, optical purity 98.6% e.e., specific rotation [α]D20 +11.1°(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-b80f23c6b4e8453bb4a08836a31b5ad5
Source dataset
uspto-grants-2000_11
Patent number
US06143908

Reaction notes

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