Water → HCID 23016512, compound

HRID 417819Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[O:11]1[CH2:15][CH2:14][CH2:13]C1.[CH2:16]([Li])CCC.O>CCCCCC>[C:15]([C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6])(=[O:11])[CH:14]([CH3:16])[CH3:13]

Participants

Conditions

Temperature: -70 °C

Procedure

A mixture comprising 2.48 g of m-iodobenzoic acid and 40 ml of tetrahydrofuran was cooled to −70° C., then 13.8 ml of n-butyllithium (1.6 M-n-hexane solution) was dropwise added over a period of 10 minutes, followed by stirring at the same temperature for 30 minutes. Then, a mixture comprising 1.5 g of N-isobutyrylpropyleneimine and 5 ml of tetrahydrofuran was added thereto at −70° C., and then the temperature was raised to room temperature, and a reaction was carried out overnight. After completion of the reaction, the reaction mixture was added to 100 ml of water and stirred, and then hexane was added thereto, followed by liquid separation. The aqueous layer was acidified by concentrated hydrochloric acid and then extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, followed by concentration under reduced pressure to obtain a crude product of m-isobutyrylbenzoic acid.

Workup

temperatureat −70° C., and then the temperature was raised to room temperature
waita reaction was carried out overnight
customAfter completion of the reaction
stirringstirred
customfollowed by liquid separation
extractionextracted with ethyl acetate
dry with materialThe extract was dried over anhydrous sodium sulfate
concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record: ord-b3b82b8e18eb4c71a90ae3685d35f0ce
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093241B2

Reaction notes

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