Water → HCID 59410080, compound

HRID 2404857Notes

Reaction equation

HRID 2404857 reaction equation
C(=O)([O-])OC[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([CH2:13][CH3:14])=[CH:6][C:5]=1[C:15]([CH3:18])([CH3:17])[CH3:16].[OH-:21].[K+].O>CO>[C:15]([C:5]1[CH:6]=[C:7]([CH2:13][CH3:14])[C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=1[OH:21])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 68462917HCID 68462917, compound

Product 1

HCID 59410080HCID 59410080, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2-tert-butyl-4-ethyl-5-nitro-phenyl)methyl carbonate (3.9 g, 13.86 mmol) in methanol (100 mL) was added KOH (1.8 g, 32.08 mmol) at room temperature. The mixture was stirred overnight. Water was added and the reaction mixture was extracted with EtOAc (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated under vacuum to give 2-tert-butyl-4-ethyl-5-nitrophenol (2.8 g, 91%), which was used in the next step without further purification.

Workup

  1. extractionthe reaction mixture was extracted with EtOAc (50 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-d0190af7cfea4796a11c7ed2e776a1a8
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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