Pyridine → Pivalic anhydride

HRID 422888Notes

Reaction equation

HRID 422888 reaction equation
N1[CH:6]=[CH:5][CH:4]=CC=1.[N+](C1C=CC(C[C:17]([OH:19])=[O:18])=CC=1)([O-])=O.[CH3:20][C:21]([CH3:26])([CH3:25])[C:22](Cl)=[O:23].[C:27]1(C)C=CC=CC=1>>[CH3:20][C:21]([CH3:26])([CH3:25])[C:22]([O:19][C:17](=[O:18])[C:5]([CH3:4])([CH3:6])[CH3:27])=[O:23]

Participants

5

Reactant 4

HCID 1049PyridineHCID 1140TolueneHCID 4661(4-Nitrophenyl)acetic acidHCID 62493Pivaloyl chloride

Product 1

HCID 15234Pivalic anhydride

Procedure

Pyridine (14 g, 0.18 Mol) and 4-nitrophenylacetic acid (32 g, 0.18 Mol) were stirred in toluene (100 ml) whilst trimethylacetylchloride (21 g, 0.18 Mol) was added. The toluene was evaporated to yield 4-nitrophenylacetic trimethylacetic anhydride. 3-Aminophenol (20 g, 0.18 Mol) was stirred in DMF (100 ml) and treated with the mixed anhydride and pyridine (14 g) in dimethylformamide (DMF) dropwise. The solution was diluted with water and the product isolated by filtration and dried (19 g, 39%).

Workup

  1. additionwas added
  2. customThe toluene was evaporated

Sources & evidence

ORD record
ord-100648e8dce54576b66da962d66c9e02
Source dataset
uspto-grants-2012_01
Patent number
US08101655B2

Reaction notes

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