Sulfuric Acid → 1,3,3-Trimethyl-3,4-dihydroisoquinoline

HRID 2224650Notes

Reaction equation

HRID 2224650 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7](O)([CH3:15])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:17](#[N:19])[CH3:18]>C1C=CC=CC=1>[CH3:18][C:17]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][C:7]([CH3:15])([CH3:6])[N:19]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 75312-Methyl-1-phenyl-2-propanol

Product 1

HCID 5941611,3,3-Trimethyl-3,4-dihydroisoquinoline

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a concentrated sulfuric acid (10 ml) was added a solution of 2-methyl-1-phenylpropan-2-ol (7.0 g) and acetonitrile (1.62 ml) in benzene (7.0 ml) dropwise at 0° C. and the mixture was stirred for 24 hours at room temperature. The reaction mixture was neutralized by adding dropwise to a mixture of ice and a saturated aqueous solution of sodium bicarbonate and the mixture was extracted with ethyl acetate twice. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in ether and thereto was added a 5N aqueous solution of sodium hydroxide and was extracted with 1N hydrochloric acid and a 2N hydrochloric acid. The extract was washed with ether and thereto was added a 5N aqueous solution of sodium hydroxide and was extracted with ether twice. The extract was washed with water and brine successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound (2.53 g) having the following physical data.

Workup

  1. additionby adding dropwise to a mixture of ice
  2. extractiona saturated aqueous solution of sodium bicarbonate and the mixture was extracted with ethyl acetate twice
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ether
  6. additionwas added a 5N aqueous solution of sodium hydroxide
  7. extractionwas extracted with 1N hydrochloric acid
  8. washThe extract was washed with ether
  9. additionwas added a 5N aqueous solution of sodium hydroxide
  10. extractionwas extracted with ether twice
  11. washThe extract was washed with water and brine successively
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1dc9afc1058649d291257bf27a89ea47
Source dataset
uspto-grants-2008_05
Patent number
US07378428B2

Reaction notes

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