Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Pivalaldehyde | HCID 12417 | — |
| Reactant | L-Lactic Acid | HCID 107689 | — |
| Reactant | p-Toluenesulfonic acid monohydrate | HCID 521998 | — |
| Catalyst | Sulfuric Acid | HCID 1118 | — |
| Solvent | Pentane | HCID 8003 | — |
| Product | 81037-06-1 | HCID 9920448 | — |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06133292 |
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| Source dataset | uspto-grants-2000_10 |
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| ORD ID | ord-bcb48caa87724b93b95a090183df350b |
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| Source note | uspto-grants-2000_10 |
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