Pyridine → HCID 66603210, compound

HRID 732642Notes

Reaction equation

HRID 732642 reaction equation
[C:1](Cl)(=[O:12])[O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.ClCCl.[C:17]([O:26][CH3:27])(=[O:25])[C:18]1[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)[OH:20].N1C=CC=CC=1>C(OCC)(=O)C>[N+:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][C:1]([O:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[C:17]([O:26][CH3:27])=[O:25])=[O:12])=[CH:4][CH:5]=1)([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 1049PyridineHCID 4133Methyl SalicylateHCID 6344DichloromethaneHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 66603210HCID 66603210, compoundYield 120.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under ice-cooling, 1.0 g of 4-nitrophenyl chlorocarbonate was added portionwise to a 10 ml dichloromethane mixture of 1.3 g methyl salicylate and 0.54 ml pyridine, and stirred at room temperature for 3Hours. The reaction solution was diluted with ethyl acetate and washed with saturated sodium bicarbonate aqueous solution and saturated brine in that order, and then the organic layer was dried with anhydrous magnesium sulfate. This was concentrated under a reduced pressure, and the thus obtained residue was mixed with hexane and ethyl acetate and subjected to decantation, thereby obtaining 1.9 g of methyl 2-{[(4-nitrophenoxy)carbonyl]oxy}benzoate as a white solid.

Workup

  1. temperatureUnder ice-cooling
  2. washwashed with saturated sodium bicarbonate aqueous solution and saturated brine in that order
  3. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  4. concentrationThis was concentrated under a reduced pressure
  5. additionthe thus obtained residue was mixed with hexane and ethyl acetate

Sources & evidence

ORD record
ord-a6c0dfa913fa4076b33dfe6e8c30a943
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

Loading…