Isobutyryl chloride → HCID 86600958, compound

HRID 1788274Notes

Reaction equation

HRID 1788274 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 444305L-Tartaric acid

Product 1

HCID 86600958HCID 86600958, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

To a suspension of L-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 (27) 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-bc9f4510ccde47d884e6fab83b6a1ae2
Source dataset
uspto-grants-2009_03
Patent number
US07511158B2

Reaction notes

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