Carbon Dioxide → beta-Phenylisovaleric acid

HRID 133835

Reaction equation

HRID 133835 reaction equation
[Mg].[CH2:2](Cl)[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:5])[CH3:4].II.BrCCBr.[C:19](=[O:21])=[O:20]>O1CCCC1>[CH3:4][C:3]([CH3:5])([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:2][C:19]([OH:21])=[O:20]

Participants

7

Reactant 5

HCID 280Carbon Dioxide2×HCID 807IodineHCID 78391,2-DibromoethaneHCID 68191Neophyl chloride2×HCID 5462224Magnesium

Product 1

HCID 13890beta-Phenylisovaleric acidYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Following a literature procedure, (Leffler, J. E.; Barbas, J. T. JACS. 1981, 103(26), 7768-7773), to a mixture of magnesium turnings (9.5 g) and neophyl chloride (7.5 mL) in tetrahydrofuran (100 mL) is added a spatula tip of iodine and 1,2-dibromoethane (1 mL). The mixture is heated gently with under a heat gun to initiate a vigorous reaction. A solution of neophyl chloride (57 mL) in tetrahydrofuran (360 mL) is added dropwise over the course of 90 minutes. Following completion of the addition, the reaction mixture is stirred for an additional five hours, then solid carbon dioxide (25 g) is added to the flask. After 10 minutes, the flask is transferred to a 40° C. water bath until all carbon dioxide had sublimed. The solvent is then removed under reduced pressure to afford the title compound (58 g, 81%) as a white paste. MS (ES+): (M+H)=178.8

Workup

  1. temperatureThe mixture is heated gently with under a heat gun
  2. customa vigorous reaction
  3. additioncompletion of the addition
  4. waitAfter 10 minutes
  5. customis transferred to a 40° C.
  6. customThe solvent is then removed under reduced pressure

Sources & evidence

ORD record
ord-83009e25d2724ee08cd2ee2fd96be188
Source dataset
uspto-grants-2008_06
Patent number
US07390910B2

Linked notes

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