Water → 81037-06-1

HRID 367364Notes

Reaction equation

HRID 367364 reaction equation
[C:1]([OH:6])(=[O:5])[C@H:2]([CH3:4])[OH:3].[CH:7](=O)[C:8]([CH3:11])([CH3:10])[CH3:9].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>OS(O)(=O)=O.CCCCC>[C:8]([C@@H:11]1[O:5][C:1](=[O:6])[C@H:2]([CH3:4])[O:3]1)([CH3:10])([CH3:9])[CH3:7]

Participants

7

Reactant 4

HCID 962WaterHCID 12417PivalaldehydeHCID 107689L-Lactic AcidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 992044881037-06-1

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 8003PentaneSolvent

Conditions

Temperature
-80 °C

Procedure

A mixture of L-Lactic acid (106 g of 85% in H2O), pivalaldehyde (220 mL), p-toluene sulfonic acid mono hydrate (2.0 g) and H2SO4 conc. (8 drops) in pentane (800 mL) was refluxed with azeotropic removal of the water formed using a Dean-Stark trap. The supernatant was decanted, washed with water, dried over MgSO4 and concentrated. The resulting residue was dissolved in hexane (800 mL) and cooled to -80° C. for 20 h. Crystals were collected by filtration in a cold room (5° C.) and washed with cold hexane (-78° C.). The crystals were dissolved in Et2O, dried over MgSO4 and concentred to give the title compound as a colorless oil. 1H NMR(CD3COCD3): δ0.95 (9H, s), 1.38 (3H,d), 4.47 (1H, m), 5.24 (1H, s).

Workup

  1. customformed
  2. customThe supernatant was decanted
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. dissolutionThe resulting residue was dissolved in hexane (800 mL)
  7. filtrationCrystals were collected by filtration in a cold room (5° C.)
  8. washwashed with cold hexane (-78° C.)
  9. dissolutionThe crystals were dissolved in Et2O
  10. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-bcb48caa87724b93b95a090183df350b
Source dataset
uspto-grants-2000_10
Patent number
US06133292

Reaction notes

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