Pyridine → Methyl 4-[(chlorocarbonyl)oxy]benzoate

HRID 1421367Notes

Reaction equation

HRID 1421367 reaction equation
[C:1](Cl)([Cl:3])=[O:2].[CH3:5][O:6][C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:3][C:1]([O:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]([O:6][CH3:5])=[O:15])=[CH:9][CH:10]=1)=[O:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6371PhosgeneHCID 7456Methylparaben

Product 1

HCID 854163Methyl 4-[(chlorocarbonyl)oxy]benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A 20% solution of phosgene (170 mL, 0.33 mol) in toluene was added to a 500 mL pear-shaped flask (flame-dried, N2). To the flask was added methyl-p-hydroxybenzoate (42.6 g, 0.28 mol) with stirring. Through an addition funnel was added pyridine (26.7 mL, 0.33 mol) in toluene while the reaction mixture was cooled in an ice bath so that the temperature did not exceed 20° C. The solution turned a yellowish color during the addition. The reaction mixture was stirred for 3 h, at which point the mixture was filtered on a buchner funnel. The pyridinium salts were washed with toluene (150 mL) and the combined organic phase washed with 1 N HCl (2×), water (2×), dried over CaCI2 and Na2SO4, and the toluene removed in vacuo to yield yellowish crystals. After continued drying, the product (38 g, 63%) turned a greyish color. m.p. 52-53° C. (lit. 51-52° C.).

Workup

  1. dry with material(flame-dried, N2)
  2. temperaturewas cooled in an ice bath so that the temperature
  3. customdid not exceed 20° C
  4. additionduring the addition
  5. stirringThe reaction mixture was stirred for 3 h, at which point the mixture
  6. filtrationwas filtered on a buchner funnel
  7. washThe pyridinium salts were washed with toluene (150 mL)
  8. washthe combined organic phase washed with 1 N HCl (2×), water (2×)
  9. dry with materialdried over CaCI2 and Na2SO4
  10. customthe toluene removed in vacuo
  11. customto yield yellowish crystals
  12. customAfter continued drying
  13. customm.p. 52-53° C. (lit. 51-52° C.)

Sources & evidence

ORD record
ord-4306e441833c46abb49e6167519d5a8f
Source dataset
uspto-grants-2000_06
Patent number
US06075141

Reaction notes

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