Water → HCID 13748711, compound

HRID 1398273Notes

Reaction equation

HRID 1398273 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].N1C=CC=CC=1.[C:26](Cl)(=[O:28])[CH3:27].O>CC(C)=O>[C:26]([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:28])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 9838158n-Octanoyl-5-salicylic acid

Product 1

HCID 13748711HCID 13748711, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

6 g (22.7 mmol) of 2-hydroxy-5-octanoylbenzoic acid and 12 mL (0.145 mol) of pyridine are dissolved in 15 mL of acetone. The medium is cooled to 0° C., and 12 mL (0.166 mol) of acetyl chloride are then added dropwise. After stirring for 15 hours at room temperature, water is added and the mixture is extracted with dichloromethane. The organic phase is dried over magnesium sulfate, filtered and then concentrated. 7 g of 2-acetyloxy-5-octanoylbenzoic acid are obtained in the form of a white solid in quantitative yield.

Workup

  1. extractionthe mixture is extracted with dichloromethane
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-989611ec287841aa962bf3592c7b1ae5
Source dataset
uspto-grants-2014_12
Patent number
US08901357B2

Reaction notes

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