Propanoic acid, 2-bromo-2-methyl-, ethyl ester → Propanoic acid, 2-(4-cyanophenoxy)-2-methyl-, ethyl ester

HRID 1073939Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].Br[C:13]([CH3:20])([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>CN(C)C=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][C:13]([CH3:20])([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:5][CH:4]=1)#[N:2]

Participants

Conditions

Temperature: 100 °C

Procedure

23.8 g of 4-cyanophenol in 150 ml of dimethylformamide were added dropwise to a stirred suspension of 6 g of 80% sodium hydride in 100 ml of dimethylformamide and the mixture was then stirred for a further 1 hour. 39 g of ethyl bromoisobutyrate were added dropwise and the mixture was heated to 100° C. for 76 hours. The solvents were removed by evaporation and the residue was partitioned between diethyl ether and water. The organic phase was washed in succession with 2M sodium hydroxide solution and sodium chloride solution and then evaporated to give 9.4 g of ethyl 2-(4-cyanophenoxy)-2-methylpropionate in the form of a colourless viscous liquid of boiling point 115°-117° C./0.05 mmHg.

Workup

customThe solvents were removed by evaporation
customthe residue was partitioned between diethyl ether and water
washThe organic phase was washed in succession with 2M sodium hydroxide solution and sodium chloride solution
customevaporated

Sources & evidence

ORD record: ord-f586a24e231e45a2b1db5187cb88970b
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04971982

Reaction notes

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