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

HRID 967761

Reaction equation

HRID 967761 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 conc. 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 and the mixture was stirred for 24 hours at room temperature. The mixture was neutralized by adding to a mixture of ice and a saturated aqueous solution of sodium bicarbonate dropwise, and it was extracted with ethyl acetate twice. The extract was dried over anhydrous magnesium sulfate and was concentrated under reduced pressure. The residue was dissolved in ether and was extracted with 1N hydrochloric acid and 2N hydrochloric acid. The extract was washed with ether and to the mixture was added 5N aqueous solution of sodium hydroxide and was extracted with ether twice. The extract was washed with water and a saturated aqueous solution of sodium chloride successively, and dried over anhydrous magnesium sulfate and was concentrated under reduced pressure to give the title compound (2.53 g) having the following physical data.

Workup

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

Sources & evidence

ORD record
ord-66824835440342adaab41f2cbaf8d1d8
Source dataset
uspto-grants-2005_10
Patent number
US06956033B2

Linked notes

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