Sodium Hydroxide → rel-(4R,5R)-4,5-Dimethyl-2-phenyl-1,3-dioxolane

HRID 2199517Notes

Reaction equation

HRID 2199517 reaction equation
CO[CH:3]([O:10][CH3:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:12]1(C)C=CC(S([O-])(=O)=O)=C[CH:13]=1.[NH+]1C=CC=C[CH:24]=1.[OH-:29].[Na+]>C1(C)C=CC=CC=1>[CH3:12][C@@H:13]1[C@@H:11]([CH3:24])[O:10][CH:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[O:29]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 62375Benzaldehyde dimethyl acetalHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 10866906rel-(4R,5R)-4,5-Dimethyl-2-phenyl-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 300 g (3.33 mol) of 2R,3R-butanediol, 422 g (2.78 mol) of benzaldehyde dimethyl acetal and 7.0 g (27.7 mmol) of pyridinium p-toluenesulphonate in 1.2 l of toluene was heated to 50° C. At 600-800 mbar, ca. 400 ml of distillate were taken off over the course of 3 hours. It was cooled and the reaction mixture was added to 500 ml of a 1 M sodium hydroxide solution. The phases were separated and the organic phase was washed twice with in each case 500 ml of water. The organic phase was dried azeotropically, with ca. 250 ml of toluene being distilled off.

Workup

  1. customwere taken off over the course of 3 hours
  2. temperatureIt was cooled
  3. customThe phases were separated
  4. washthe organic phase was washed twice with in each case 500 ml of water
  5. dry with materialThe organic phase was dried azeotropically, with ca. 250 ml of toluene being
  6. distillationdistilled off

Sources & evidence

ORD record
ord-ccd0590339da468496ebaa047a936f4e
Source dataset
uspto-grants-2016_06
Patent number
US09359306B2

Reaction notes

Loading…