Isobutyryl chloride → HCID 86600959, compound

HRID 1765490Notes

Reaction equation

HRID 1765490 reaction equation
[C:1]([OH:10])(=[O:9])[C@H:2]([C@@H:4]([C:6]([OH:8])=O)[OH:5])[OH:3].[C:11](Cl)(=[O:15])[CH:12]([CH3:14])[CH3:13]>C1(C)C=CC=CC=1.CCOCC.CCCCCC>[O:10]=[C:1]1[C@@H:2]([O:3][C:11](=[O:15])[CH:12]([CH3:14])[CH3:13])[C@H:4]([O:5][C:11](=[O:15])[CH:12]([CH3:14])[CH3:13])[C:6](=[O:8])[O:9]1

Participants

6

Reactant 2

HCID 62325Isobutyryl chlorideHCID 439655D-Tartaric acid

Product 1

HCID 86600959HCID 86600959, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

To a suspension of D-tartaric acid (5.0 g, 33.3 mmol) in toluene (60 mL) was added isobutyryl chloride (11.3 mL, 107 mmol). The resulting suspension was heated to reflux and stirred for 22 h at reflux temperature. The reaction mixture was then concentrated in vacuo to afford a crystalline solid, which was suspended in a mixture of ether and hexane (1:3), filtered, washed with hexane and dried to afford the desired compound (30) as a white crystalline solid (6.4 g, 71%). 1H-NMR (400 MHz, CDCl3): δ 1.25 (d, J=6.8 Hz, 12H), 2.72 (hept, J=6.8 Hz, 2H), 5.63 (s, 2H).

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux
  3. temperatureat reflux temperature
  4. concentrationThe reaction mixture was then concentrated in vacuo
  5. customto afford a crystalline solid, which
  6. filtrationfiltered
  7. washwashed with hexane
  8. customdried

Sources & evidence

ORD record
ord-e042327b29504fe9bea5d340fd39420c
Source dataset
uspto-grants-2007_06
Patent number
US07227028B2

Reaction notes

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