4-Nitrophenol → 4-Nitrophenyl trimethylacetate

HRID 1700274Notes

Reaction equation

HRID 1700274 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O-:10])=[O:9]>N1C=CC=CC=1>[C:2]([C:1]([O:17][C:14]1[CH:15]=[CH:16][C:11]([N+:8]([O-:10])=[O:9])=[CH:12][CH:13]=1)=[O:6])([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 9804-NitrophenolHCID 62493Pivaloyl chloride

Product 1

HCID 778594-Nitrophenyl trimethylacetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

161.1 mmol (19.48 g) of pivaloyl chloride are added, at 0° C., to a solution of 107.8 mmol (15 g) of 4-nitrophenol in 250 ml of pyridine. The reaction mixture is stirred for 72 hours at ambient temperature. The reaction mixture is evaporated in vacuo and the oily residue is diluted with ethyl acetate and then washed with aqueous hydrochloric acid solution (0.1N) and then with 10% aqueous sodium chloride solution. The expected product is obtained by drying the organic phase and then concentrating.

Workup

  1. customThe reaction mixture is evaporated in vacuo
  2. additionthe oily residue is diluted with ethyl acetate
  3. washwashed with aqueous hydrochloric acid solution (0.1N)

Sources & evidence

ORD record
ord-b0bec8bf94a64b0891997186b50fd2e4
Source dataset
uspto-grants-2002_02
Patent number
US06350759B1

Reaction notes

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