Hydrochloric Acid → 3,3-Dimethyl-1-(2-nitrophenyl)butan-2-ol

HRID 656800Notes

Reaction equation

HRID 656800 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10])([O-:3])=[O:2].[OH-].[K+].[CH:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15].Cl>CN(C=O)C>[CH3:15][C:14]([CH3:17])([CH3:16])[CH:13]([OH:18])[CH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 69442-NitrotolueneHCID 12417Pivalaldehyde3×HCID 14797Potassium Hydroxide

Product 1

HCID 592538163,3-Dimethyl-1-(2-nitrophenyl)butan-2-olYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 153.9 g (1.12 mol) of 2-nitrotoluene in 900 ml of DMF are added, within one hour, 4.5 g (80.2 mmol) of KOH and simultaneously 193.3 g (2.24 mol) of pivalaldehyde. Subsequently, first a further 0.5 equivalent of pivalaldehyde is added and the mixture is stirred at RT for one hour, then another 0.5 equivalent of pivalaldehyde is added and the mixture is stirred at room temperature for a further 2 hours. The mixture is acidified with 40 ml of 10 percent aqueous hydrochloric acid until the color changes (pH 4.5) and a majority of the DMF is distilled off under reduced pressure. After the residue has been distilled at 130° C./0.9 mbar, 136.8 g (yield 54% of theory, purity (GC-MS 98%) of 3,3-dimethyl-1-(2-nitrophenyl)butan-2-ol are obtained.

Workup

  1. stirringthe mixture is stirred at room temperature for a further 2 hours
  2. distillationa majority of the DMF is distilled off under reduced pressure
  3. distillationAfter the residue has been distilled at 130° C./0.9 mbar, 136.8 g (yield 54% of theory, purity (GC-MS 98%) of 3,3-dimethyl-1-(2-nitrophenyl)butan-2-ol
  4. customare obtained

Sources & evidence

ORD record
ord-36dfb98d33dc4519963ab3e80d23c9fb
Source dataset
uspto-grants-2011_12
Patent number
US08071824B2

Reaction notes

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