Salicylic Acid → Carbonic acid, ethyl ester, ester with salicylic acid

HRID 511912Notes

Reaction equation

HRID 511912 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].CN(C)C1C=CC=CC=1.Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C1(C)C=CC=CC=1>[CH2:24]([O:23][C:21]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([OH:10])=[O:9])=[O:22])[CH3:25]

Participants

5

Reactant 3

HCID 338Salicylic AcidHCID 949N,N-DimethylanilineHCID 10928Ethyl chloroformate

Product 1

HCID 26578Carbonic acid, ethyl ester, ester with salicylic acidYield 42%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

60 g (434 mmol) of salicylic acid and 111 ml of N,N-dimethylaniline are dissolved in 360 ml of toluene. The medium is cooled to 0° C. and then 41.5 ml (434 mmol) of ethyl chloroformate are added dropwise. After stirring for 2 hours at ambient temperature, the mixture is washed with a 1N aqueous hydrochloric acid solution and then with a saturated sodium chloride solution. The organic phase is dried over magnesium sulphate, filtered and concentrated. The residue is taken up in dichloromethane and precipitated from heptane. The solid is filtered off and then dried. 38 g of 2-(ethoxycarbonyloxy)benzoic acid are obtained in the form of a white solid with a yield of 42%.

Workup

  1. washthe mixture is washed with a 1N aqueous hydrochloric acid solution
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customprecipitated from heptane
  6. filtrationThe solid is filtered off
  7. customdried

Sources & evidence

ORD record
ord-1af36406220d49f09d3f1fe803c00f17
Source dataset
uspto-grants-2015_08
Patent number
US09102607B2

Reaction notes

Loading…