Sulfuric Acid → 4-(Dimethylamino)-4-(4-methoxyphenyl)cyclohexan-1-one

HRID 76943Notes

Reaction equation

HRID 76943 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([N:19]([CH3:21])[CH3:20])[CH2:18][CH2:17][C:12]3(OCC[O:13]3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.OS(O)(=O)=O>CCOCC>[CH3:20][N:19]([CH3:21])[C:9]1([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:18][CH2:17][C:12](=[O:13])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 12595623[8-(4-Methoxy-phenyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-dimethylamine

Product 1

HCID 125956454-(Dimethylamino)-4-(4-methoxyphenyl)cyclohexan-1-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The title compound from step 1 (6.80 g, 23 mmol) was dissolved in ether (100 mL), mixed with 5% H2SO4 (100 mL) and the solution vigorously stirred for 2 d at RT. The phases were separated and the ether phase discarded. The aqueous phase was made alkaline with 5N NaOH with ice cooling and extracted three times with ether, the combined organic phases were then washed with water, dried over Na2SO4 and concentrated to low volume in a vacuum.

Workup

  1. customThe phases were separated
  2. extractionextracted three times with ether
  3. washthe combined organic phases were then washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to low volume in a vacuum

Sources & evidence

ORD record
ord-babd786c1e554bcb90455b8ce9dd13fb
Source dataset
uspto-grants-2014_09
Patent number
US08835689B2

Reaction notes

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