Methyl chloroformate → Benzoic Acid

HRID 2051607Notes

Reaction equation

HRID 2051607 reaction equation
ClC1C=NC(OCC2CCCCC2)=C(C=1)C(O)=O.COC(Cl)=O.[Na].NCC[C:28]1[CH:36]=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][CH:29]=1.C([O-])(=O)C.[Na+]>O1CCCC1.C(N(CC)CC)C>[C:32]([OH:34])(=[O:33])[C:31]1[CH:35]=[CH:36][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 517045Sodium AcetateHCID 20379241HCID 20379241, compoundHCID 705908304-(2-Aminoethyl)-benzoic acid sodium

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

1 g of triethylamine is added to 2.7 g of 5-chloro-2-hexahydrobenzyloxy-nicotinic acid (melting point 150° to 151° C., prepared from 2-chloronicotinic acid by reacting same with hexahydrobenzyl alcohol-sodium with subsequent chlorination with chlorine) in 100 ml of tetrahydrofuran and, after cooling to 0° C., 0.95 g of chloroformic acid methyl ester is added. Stirring of the mixture is continued for 15 minutes at 0° C. and the mixture is added to 10 ml of an about 1 molar solution of 4-(2-aminoethyl)-benzoic acid sodium additionally containing 0.01 mol of sodium acetate, and stirring is continued for 3 hours at room temperature. The major proportion of the solvent is distilled off under reduced pressure and the residue is acidified. The 4-(2-<5-chloro-2-hexahydrobenzyloxy-nicotinamido>-ethyl)-benzoic acid obtained is reprecipitated from ammonia and recrystallized from dilute ethanol. Melting point 177°-178° C.

Workup

  1. stirringstirring
  2. waitis continued for 3 hours at room temperature
  3. distillationThe major proportion of the solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-8b41fe22415d419f8e0edbd64e9ac130
Source dataset
uspto-grants-1980_01
Patent number
US04181658

Reaction notes

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