Water → HCID 19372075, compound

HRID 129659Notes

Reaction equation

HRID 129659 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([CH3:17])([CH3:16])[C:12]([O:14][CH3:15])=[O:13].[C:18]1(=[O:28])[NH:22][C:21](=[O:23])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12.[K].O>CN(C)C=O>[C:18]1(=[O:28])[N:22]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([CH3:17])([CH3:16])[C:12]([O:14][CH3:15])=[O:13])[C:21](=[O:23])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12

Participants

5

Reactant 3

HCID 962WaterHCID 19372027HCID 19372027, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 19372075HCID 19372075, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

12.3 g of methyl 11-bromo-2,2-dimethylundecanoate in solution in 70 cm3 of N,N-dimethylformamide are added to 8.2 g of potassium phthalimide in 70 cm3 of N,N-dimethylformamide and the mixture is heated for 3 hours at a temperature in the region of 80° C. The solution is cooled to a temperature in the region of 20° C. and then poured into 1400 cm3 of distilled water. Acidification is carried out to a pH in the region of 2 using 4N hydrochloric acid and extraction is then carried out with a total of 1000 cm3 of ethyl acetate. The organic phase is washed with a total of 450 cm3 of distilled water, dried over magnesium sulphate, and then concentrated under reduced pressure (13.5 Pa) at a temperature in the region of 60° C. 15.4 g of methyl 11-phthalimido-2,2-dimethylundecanoate are thus obtained in the form of a pale yellow viscous oil [Rf =0.38; silica thin layer chromatography; eluent: cyclohexane/ethyl acetate 8/2 (by volume)].

Workup

  1. temperatureThe solution is cooled to a temperature in the region of 20° C.
  2. extractionAcidification is carried out to a pH in the region of 2 using 4N hydrochloric acid and extraction
  3. washThe organic phase is washed with a total of 450 cm3 of distilled water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure (13.5 Pa) at a temperature in the region of 60° C

Sources & evidence

ORD record
ord-9155643392d24aaf93d4caf7a876ff5e
Source dataset
uspto-grants-1995_11
Patent number
US05468888

Reaction notes

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