Water → HCID 59410080, compound

HRID 1915460Notes

Reaction equation

HRID 1915460 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-e2409e6f99164c85a3abd959624a1253
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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