Hydrochloric Acid → 1-(2-Nitrophenyl)-2,2-dimethyl-1-propanol

HRID 333471Notes

Reaction equation

HRID 333471 reaction equation
[C@]12(C)C(C)(C)C(CC1)CC2C([O:12][CH:13]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25])[C:14]([CH3:17])([CH3:16])[CH3:15])=O.C([O-])([O-])=O.[K+].[K+].O.Cl>CO>[N+:24]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH:13]([OH:12])[C:14]([CH3:16])([CH3:15])[CH3:17])([O-:26])=[O:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 86639080HCID 86639080, compound

Product 1

HCID 591895461-(2-Nitrophenyl)-2,2-dimethyl-1-propanolYield 92.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of single diastereomer (R or S)-1-(2-nitrophenyl)-2,2-dimethyl-1-propyl (1S)-camphanate (658 mg, 1.68 mmol) and K2CO3 (241 mg, 1.74 mmol) in methanol (23 mL) was heated to reflux for 30 minutes. Water (5 mL) was added and the solution was neutralized to pH 7 with 1M HCl. Solvent was removed in vacuo and the residue was taken into a mixture of ethyl acetate (20 mL) and water (10 mL). The organic phase was separated, dried over anhydrous Na2SO4, concentrated in vacuo and purified by silica gel column chromatography to yield single enantiomer (R or S)-1-(2-nitrophenyl)-2,2-dimethyl-1-propanol (325 mg, 92%) as a light yellow oil. 1H NMR was identical to that of the racemic alcohol. The absolute configuration of the single enantiomer alcohol is not determined.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 30 minutes
  3. customSolvent was removed in vacuo
  4. additionthe residue was taken into a mixture of ethyl acetate (20 mL) and water (10 mL)
  5. customThe organic phase was separated
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-4204de23e1fd4da08725eb6472ffef1e
Source dataset
uspto-grants-2014_11
Patent number
US08877905B2

Reaction notes

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