Salicylic Acid → HCID 21481530, compound

HRID 511922Notes

Reaction equation

HRID 511922 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].N1C=CC=CC=1.[CH3:17][C:18]([CH3:23])([CH3:22])[C:19](Cl)=[O:20].O>CC(C)=O>[CH3:17][C:18]([CH3:23])([CH3:22])[C:19]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([OH:10])=[O:9])=[O:20]

Participants

6

Reactant 4

HCID 338Salicylic AcidHCID 962WaterHCID 1049PyridineHCID 62493Pivaloyl chloride

Product 1

HCID 21481530HCID 21481530, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

10 g (72.4 mmol) of salicylic acid and 6.1 ml (76 mmol) of pyridine are placed in 100 ml of acetone at −5° C. 9.3 ml (76 mmol) of 2,2-dimethylpropionyl chloride are added and, after stirring at ambient temperature for 2 hours, water is added and the mixture is extracted with dichloromethane. The organic phase is dried over magnesium sulphate, filtered and concentrated. The residue is precipitated from heptane at 0° C. and then filtered off. 16.9 g of 2-(2,2-dimethylpropionyloxy)benzoic acid are obtained in the form of a white powder with a yield of 95%.

Workup

  1. extractionthe mixture is extracted with dichloromethane
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is precipitated from heptane at 0° C.
  6. filtrationfiltered off

Sources & evidence

ORD record
ord-2555f5ff7aee4849ae3c999d102b7c09
Source dataset
uspto-grants-2015_08
Patent number
US09102607B2

Reaction notes

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