N,N-Dimethylaniline → HCID 86680239, compound

HRID 1398276Notes

Reaction equation

HRID 1398276 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([C:11](=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CN(C)C1C=CC=CC=1.Cl[C:30]([O:32][CH2:33][CH3:34])=[O:31]>C1(C)C=CC=CC=1>[CH2:33]([O:32][C:30]([O:1][C:2]1[CH:10]=[CH:9][C:8]([C:11](=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])=[O:31])[CH3:34]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 10928Ethyl chloroformateHCID 9838158n-Octanoyl-5-salicylic acid

Product 1

HCID 86680239HCID 86680239, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

4.89 g (18.50 mmol) of 2-hydroxy-5-octanoylbenzoic acid and 9 ml (70.30 mmol) of N,N-dimethylaniline are dissolved in 30 ml of toluene. The medium is cooled to 0° C., and 1.77 ml (18.50 mmol) of ethyl chloroformate are then added dropwise. After stirring for 2 hours at room temperature, the mixture is washed with aqueous 0.5N hydrochloric acid solution and then with water. The organic phase is dried over magnesium sulfate, filtered and concentrated. 5.59 g of 2-ethoxycarbonyloxy-5-octanoylbenzoic acid are obtained in the form of a white solid in a yield of 89%.

Workup

  1. washthe mixture is washed with aqueous 0.5N hydrochloric acid solution
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-72274d42664448a984d0faea2aafaedb
Source dataset
uspto-grants-2014_12
Patent number
US08901357B2

Reaction notes

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