Hydrochloric Acid → 5-Chloro-2-dodecyl-1-naphthalenol

HRID 1834535

Reaction equation

HRID 1834535 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:13](=O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:7]2[OH:12].Cl>[Zn].C(O)C>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:7]2[OH:12]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 213252361-(5-Chloro-1-hydroxynaphthalen-2-yl)-1-dodecanone

Product 1

HCID 213252425-Chloro-2-dodecyl-1-naphthalenol

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

A solution of 17.4 parts of 1-(5-chloro-1-hydroxynaphthalen-2-yl)-1-dodecanone and 107 parts of 37% hydrochloric acid in 2.5 parts of ethanol was contacted with stirring at reflux during 26 hours, with 40 parts of zinc dust which has been amalgamated by treatment with 3 parts of mercuric chloride and 53 parts of 2.1% hydrochloric acid followed by washing with ethanol. The zinc amalgam was added in small portions throughout the reaction period. Upon cooling, a solid separated. After dissolution of this solid in ethanol, zinc amalgam was filtered, and cooling gave 0.5 parts of starting material which was filtered. Concentration of the filtrate, purification by recrystallization from ethanol, and column chromatography on silica gel using 1-chlorobutane as eluent gave 12 parts of 5-chloro-2-dodecyl-1-naphthalenol, m.p. 68°-70° C.

Workup

  1. washby washing with ethanol
  2. additionThe zinc amalgam was added in small portions throughout the reaction period
  3. temperatureUpon cooling
  4. customa solid separated
  5. dissolutionAfter dissolution of this solid in ethanol
  6. filtrationzinc amalgam was filtered
  7. temperaturecooling
  8. customgave 0.5 parts of starting material which
  9. filtrationwas filtered
  10. customConcentration of the filtrate, purification
  11. customby recrystallization from ethanol, and column chromatography on silica gel

Sources & evidence

ORD record
ord-83bc1208dcd94ea7911883ce3b2221bc
Source dataset
uspto-grants-1978_01
Patent number
US04070481

Linked notes

Loading…