Ammonium Chloride → 1-(4-tert-Butylphenyl)ethanol

HRID 576058Notes

Reaction equation

HRID 576058 reaction equation
[CH3:1][Mg]Br.[C:4]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1)([CH3:7])([CH3:6])[CH3:5].[Cl-].[NH4+]>C(OCC)C>[C:4]([C:8]1[CH:9]=[CH:10][C:11]([CH:12]([OH:13])[CH3:1])=[CH:14][CH:15]=1)([CH3:7])([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 703244-tert-ButylbenzaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 2607311-(4-tert-Butylphenyl)ethanolYield 103.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methylmagnesium bromide (3 mol/L diethyl ether solution, 5 mL, 15.0 mmol) was added dropwise to a solution of 4-tert-butylbenzaldehyde (1.62 g, 10.0 mmol) in diethyl ether (20 mL) while cooling in ice, and the mixture was stirred at the same temperature for 30 min. Aqueous ammonium chloride solution was added thereto and the mixture was extracted with diethyl ether. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The desiccant was filtered off and then the filtrate was concentrated under reduced pressure to afford 1-(4-tert-butylphenyl)ethanol as a colorless solid (1.84 g).

Workup

  1. temperaturewhile cooling in ice
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe desiccant was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-eec4222b514c48ceacd93e174b144623
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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