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

HRID 274820Notes

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

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

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

Sources & evidence

ORD record: ord-fb3bbd8f7b50413883dd4b02e8210617
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE034865

Reaction notes

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