Benzene → 1-[Bis(hydroxymethyl)-methyl]-6,7-dimethoxy-3,4-dihydroisoquinoline

HRID 542191

Reaction equation

HRID 542191 reaction equation
[CH2:1]=[O:2].C1C=CC=CC=1.[CH3:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[CH2:13][CH2:12][N:11]=1.C[CH2:25][O-:26].[Na+]>>[OH:2][CH2:1][CH:9]([CH2:25][OH:26])[C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[CH2:13][CH2:12][N:11]=1

Participants

5

Reactant 4

HCID 241BenzeneHCID 712FormaldehydeHCID 226523,4-Dihydro-6,7-dimethoxy-1-methylisoquinolineHCID 2723922Sodium ethoxide

Product 1

HCID 136966801-[Bis(hydroxymethyl)-methyl]-6,7-dimethoxy-3,4-dihydroisoquinoline

Procedure

To a solution of 2.5 moles of paraformaldehyde in 500 ml. of benzene 1 mole (205.3 g) of 1-methyl-6,7-dimethoxy-3,4-dihydroisoquinoline and subsequently freshly prepared sodium ethylate (1 g sodium+50 ml ethanol) are added at room temperature, with stirring. The reaction mixture is refluxed for 4 hours. The mixture is then evaporated under reduced pressure, and the obtained crystalline material is recrystallized from a mixture of acetone and ether. The aimed compound is obtained which has the same melting point as the product prepared in Example 1.

Workup

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. customThe mixture is then evaporated under reduced pressure
  3. customthe obtained crystalline material is recrystallized from a mixture of acetone and ether

Sources & evidence

ORD record
ord-275bef7252a34716816043ec5c21bea5
Source dataset
uspto-grants-1987_04
Patent number
US04656179

Linked notes

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