Carbon Dioxide → beta-Phenylisovaleric acid

HRID 1610671Notes

Reaction equation

HRID 1610671 reaction equation
[Mg].II.Cl[CH2:5][C:6]([CH3:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:7].BrCCBr.[C:19](=[O:21])=[O:20].Cl>O1CCCC1.O>[CH3:7][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:14])[CH2:5][C:19]([OH:21])=[O:20]

Participants

9

Reactant 6

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 807IodineHCID 78391,2-DibromoethaneHCID 68191Neophyl chlorideHCID 5462224Magnesium

Product 1

HCID 13890beta-Phenylisovaleric acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

While stirring powdery magnesium (9.56 g, 393 mmol) and iodine (one crumb) in tetrahydrofuran (10 ml), a solution of 1-chloro-2-methyl-2-phenylpropane (26.53 g, 157.3 mmol) and 1,2-dibromoethane (29.6 g, 157 mmol) in tetrahydrofuran (100 ml) was dropwise added at a rate permitting the reaction solution to gently reflux. After completion of the dropwise addition, the mixture was stirred at 60° C. for 4 hrs. The reaction solution was cooled to −78° C., and pulverized dry ice (50 g) was carefully added. After completion of the dropwise addition, the reaction solution was gradually warmed to room temperature with stirring. The reaction solution was diluted with water, acidified with conc. hydrochloric acid, and extracted twice with ethyl acetate. The solvent of the recovered organic layer was evaporated under reduced pressure. The obtained residue was mixed with sodium hydroxide (6 g) and water (200 ml). The obtained aqueous solution was washed with diethyl ether-hexane, acidified with conc. hydrochloric acid, and extracted twice with ethyl acetate. The recovered organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to give the objective substance.

Workup

  1. temperatureto gently reflux
  2. additionAfter completion of the dropwise addition
  3. temperatureThe reaction solution was cooled to −78° C.
  4. additionwas carefully added
  5. additionAfter completion of the dropwise addition
  6. temperaturethe reaction solution was gradually warmed to room temperature
  7. stirringwith stirring
  8. extractionextracted twice with ethyl acetate
  9. customThe solvent of the recovered organic layer was evaporated under reduced pressure
  10. additionThe obtained residue was mixed with sodium hydroxide (6 g) and water (200 ml)
  11. washThe obtained aqueous solution was washed with diethyl ether-hexane
  12. extractionextracted twice with ethyl acetate
  13. dry with materialThe recovered organic layer was dried over anhydrous magnesium sulfate
  14. customthe solvent was evaporated under reduced pressure
  15. customto give the objective substance

Sources & evidence

ORD record
ord-88473e8ee69742858af0bd2a40390dd5
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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