Acetic Acid → 1-acetoxyethyl p-nitrophenyl carbonate

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: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

Reactant 2

HCID 176Acetic Acid

HCID 105383541-chloroethyl (4-nitrophenyl) Carbonate

Product 1

HCID 117805601-acetoxyethyl p-nitrophenyl carbonate

Procedure

To a solution of 10.0 g of product from Example 317 in 250 ml of acetic acid is added 15.0 g mercuric acetate. The mixture is stirred at room temperature for 22 hours, concentrated in vacuo, and purified by chromatography (Silica gel: methylene chloride -5% methyl alcohol/methylene chloride) to give 7.5 g of the desired product.

Workup

concentrationconcentrated in vacuo
custompurified by chromatography (Silica gel: methylene chloride -5% methyl alcohol/methylene chloride)

Sources & evidence

ORD record: ord-bb2b2fc1e1a54d37a1aba85639b4d2e5
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05623081

Reaction notes

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