Sulfuric Acid → Ethyl 2,2-dimethyl-3-phenylpropanoate

HRID 2372707Notes

Reaction equation

HRID 2372707 reaction equation
C([Li])CCC.Br[C:7]([CH3:14])([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.S(=O)(=O)(O)O>CCCCCC.O1CCCC1>[CH3:13][C:7]([CH3:14])([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 7498Benzyl BromideHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 178418339Butyllithium

Product 1

HCID 4684633Ethyl 2,2-dimethyl-3-phenylpropanoate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-20 °C

Procedure

25 ml of a 1.6M solution of n-butyllithium in n-hexane were added dropwise to a solution of 5.3 ml (7 g, 36 mmol) of ethyl bromoisobutyrate in 20 ml of tetrahydrofuran at -75° to -70° C. The mixture was then warmed to -20° C., 6.42 ml (9.43 g, 54 mmol) of benzylbromide were added dropwise and the mixture was subsequently stirred at room temperature for a further 3 hours. Dilute sulfuric acid was then added to the reaction mixture and the mixture was extracted twice with ether. The organic phase was washed with water, dried over magnesium sulfate and concentrated in vacuo. The crude product (6.6 g) was purified by distillation.

Workup

  1. extractionthe mixture was extracted twice with ether
  2. washThe organic phase was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. distillationThe crude product (6.6 g) was purified by distillation

Sources & evidence

ORD record
ord-3907fe5b0cad4c0cad9b5c237b1010ff
Source dataset
uspto-grants-1992_03
Patent number
US05100887

Reaction notes

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