Methyl chloroformate → Benzoic Acid

HRID 2051608Notes

Reaction equation

HRID 2051608 reaction equation
COC(Cl)=O.C(O[C:11]1N=[C:18]([CH3:20])[C:17](Cl)=[CH:16][C:12]=1[C:13]([OH:15])=[O:14])CCC.NCCC1C=CC(C(O)=O)=CC=1.[Na].C([O-])(=O)C.[Na+]>CC(C)=O.C(N(CC)CC)C>[C:13]([OH:15])(=[O:14])[C:12]1[CH:11]=[CH:20][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 517045Sodium AcetateHCID 20379237HCID 20379237, compoundHCID 705908304-(2-Aminoethyl)-benzoic acid sodium

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 8471TriethylamineSolvent

Procedure

2.8 g of triethylamine and 2.6 g of chloroformic acid methyl ester are added, while stirring and cooling with ice, to 6.1 g of 2-butoxy-5-chloro-6-methyl-nicotinic acid (melting point 95°-97° C., prepared by chlorinating 2-butoxy-6-methyl-nicotinic acid in dilute glacial acetic acid) in 75 ml of acetone. The mixture is stirred for a further 15 minutes and then added, while stirring, to 25 ml of a 1-molar solution of 4-(2-amino-ethyl)-benzoic acid-sodium, additionally containing 0.025 mol of sodium acetate and to which 25 ml of acetone has been added. Stirring of the mixture is continued for 2 hours at room temperature, the acetone is removed under reduced pressure, the remaining aqueous solution is acidified, the precipitated reaction product is filtered off with suction, reprecipitated from ammonia and recrystallized from dilute methanol or ethyl acetate. The 4-(2-<2-butoxy-5-chloro-6-methyl-nicotinamido>-ethyl)-benzoic acid obtained melts at 148°-150° C.

Workup

  1. stirringThe mixture is stirred for a further 15 minutes
  2. additionadded
  3. stirringStirring of the mixture
  4. customthe acetone is removed under reduced pressure
  5. customthe precipitated reaction product
  6. filtrationis filtered off with suction
  7. customreprecipitated from ammonia
  8. customrecrystallized from dilute methanol or ethyl acetate

Sources & evidence

ORD record
ord-cce071f07ec347b98dd8c54d8dd9d893
Source dataset
uspto-grants-1980_01
Patent number
US04181658

Reaction notes

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