Ethanol → HCID 131710909, compound

HRID 2072485Notes

Reaction equation

HRID 2072485 reaction equation
[CH2:1]1[CH2:12][C:10](=[O:11])[C:4]2[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:3]=2[CH2:2]1.[ClH:13].[CH3:14][NH:15][CH3:16].C=O.[CH2:19](O)C>CC(C)=O>[ClH:13].[F:9][C:7]1[CH:8]=[C:3]2[C:4](=[CH:5][CH:6]=1)[C:10](=[O:11])[CH:12]([CH2:14][N:15]([CH3:19])[CH3:16])[CH2:1][CH2:2]2

Participants

6

Reactant 4

HCID 702EthanolHCID 712Formaldehyde2×HCID 10473Dimethylamine, hydrochlorideHCID 149151166-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 131710909HCID 131710909, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture comprising 8.0 g 6-fluoro-α-tetralone, 5.3 g of dimethylamine hydrochloride, 2.0 g paraformaldehyde, and 10 ml 95% ethanol containing 0.1 ml concentrated hydrogen chloride is heated on a steam bath for 1.5 hours. The reaction mixture soon because homogeneous and the paraformaldehyde dissolves. The warm solution (bright yellow) is transferred to a widemouthed flask and is quickly diluted by the addition of acetone (100 ml). Cooling this solution in the freezer for 16 hours produced a crystalline mass of white plates that is collected and washed with additional acetone. After drying this material in vacuo, the crystalline title compound weighs 10.1 g (80%) melting point 152°-153° C.

Workup

  1. customThe warm solution (bright yellow) is transferred to a widemouthed flask
  2. temperatureCooling this solution in the freezer for 16 hours
  3. customproduced a crystalline mass of white plates that
  4. customis collected
  5. washwashed with additional acetone
  6. customAfter drying this material in vacuo

Sources & evidence

ORD record
ord-cf8c7cacb4534975aa8dc909b8b20513
Source dataset
uspto-grants-1977_09
Patent number
US04051248

Reaction notes

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