Toluene → HCID 54196354, compound

HRID 1885259Notes

Reaction equation

HRID 1885259 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]([Cl:12])=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].[C:13]1(C)C=CC=C[CH:14]=1>C(O)C>[CH2:13]([O:6][C:5](=[O:7])[C:4]1[C:8]([Cl:12])=[CH:9][C:10]([OH:11])=[C:2]([OH:1])[CH:3]=1)[CH3:14]

Participants

4

Reactant 2

HCID 1140TolueneHCID 198801802-Chloro-4,5-dihydroxybenzoic acid

Product 1

HCID 54196354HCID 54196354, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3,4-dihydroxy-6-chlorobenzoic acid (48 g: 250 mMol.) in a mixture of toluene (180 ml) and ethanol (180 ml) is heated under reflux under Dean Stark apparatus filled with Molecular Sieves for 12 hours. The reaction mixture is cooled and washed with aqueous sodium hydrogen carbonate and water, dried and concentrated under reduced pressure to give 6-chloro-3,4-dihydroxybenzoic acid ethyl ester (52.7 g). Yield: 95%.

Workup

  1. temperatureis heated
  2. temperatureunder reflux under Dean Stark apparatus
  3. additionfilled with Molecular Sieves for 12 hours
  4. temperatureThe reaction mixture is cooled
  5. washwashed with aqueous sodium hydrogen carbonate and water
  6. customdried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6675e24117374f5ab07500d2090a0284
Source dataset
uspto-grants-1992_09
Patent number
US05143910

Reaction notes

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