Acetic Acid → 1-acetoxyethyl p-nitrophenyl carbonate

HRID 889819Notes

Reaction equation

HRID 889819 reaction equation
[C:1](=[O:16])([O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)[O:2][CH:3](Cl)[CH3:4].[C:17]([OH:20])(=[O:19])[CH3:18]>C([O-])(=O)C.[Hg+]>[C:1](=[O:16])([O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)[O:2][CH:3]([O:20][C:17](=[O:19])[CH3:18])[CH3:4]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 105383541-chloroethyl (4-nitrophenyl) Carbonate

Product 1

HCID 117805601-acetoxyethyl p-nitrophenyl carbonate

Reagents, catalysts & solvents 1

HCID 61181Mercurous acetateCatalyst2×

Procedure

7.8 g (24.4 mmol, 1.5 eq) of mercury acetate are added to a solution of 4 g (16.3 mmol, 1 eq) of (1) dissolved in 100 ml of acetic acid. The reaction mixture is stirred for 1 day at ambient temperature, and then an additional 1 g (3.13 mmol, 0.2 eq) of mercury acetate is added. After stirring for a further 1 day at ambient temperature, the reaction is complete. The acetic acid is evaporated off under high vacuum and the residue is taken up in ether. The organic phase is extracted with a saline solution and then dried over Na2SO4, filtered and evaporated under reduced vacuum, to give a yellow oil. The crude product is chromatographed on silica gel, to give a colorless oil (4.4 g).

Workup

  1. stirringAfter stirring for a further 1 day at ambient temperature
  2. customThe acetic acid is evaporated off under high vacuum
  3. extractionThe organic phase is extracted with a saline solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced vacuum
  7. customto give a yellow oil
  8. customThe crude product is chromatographed on silica gel

Sources & evidence

ORD record
ord-0f27d39ad10d4c7abbcaa74b729c4484
Source dataset
uspto-grants-2006_02
Patent number
US06995139B2

Reaction notes

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