4-Nitrophenol → 4-Nitrophenyl 2-Chloroacetoacetate

HRID 1380640Notes

Reaction equation

HRID 1380640 reaction equation
[Cl:1][C:2]1[C:3](=[O:11])[O:4][C:5]([CH3:10])([CH3:9])[O:6][C:7]=1[CH3:8].[N+:12]([C:15]1[CH:20]=CC(O)=C[CH:16]=1)([O-:14])=[O:13]>C1(C)C(C)=CC=CC=1>[Cl:1][CH:2]([C:7]([CH3:8])=[O:6])[C:3]([O:4][C:5]1[CH:10]=[CH:20][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:9]=1)=[O:11]

Participants

4

Reactant 2

HCID 9804-NitrophenolHCID 135878355-Chloro-2,2,6-Trimethyl-1,3-Dioxin-4-One

Product 1

HCID 135878364-Nitrophenyl 2-ChloroacetoacetateYield 84.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
135 °C

Procedure

A solution of 5-chloro-2,2,6-trimethyl-4H-1,3-dioxin-4-one (8.8 g, 50 mmol) and 4-nitrophenol (7.65 g, 55 mmol) in 5 ml of xylene under continuous nitrogen purge was immersed in an oil bath preheated to 110° C. The reaction was then heated to 135° C. and then stirred an additional 15 minutes. The pale brown reaction was cooled to 20° C. and the precipitated product washed with ether/hexanes to afford 10.9 g (84%) of the title compound as flaky, white crystals.

Workup

  1. customwas immersed in an oil bath
  2. custompreheated to 110° C
  3. customThe pale brown reaction
  4. temperaturewas cooled to 20° C.
  5. washthe precipitated product washed with ether/hexanes

Sources & evidence

ORD record
ord-7afc7e44ca2147bd989d4cc567ef1bac
Source dataset
uspto-grants-1986_04
Patent number
US04582913

Reaction notes

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