1-Naphthol → HCID 53733484, compound

HRID 596407Notes

Reaction equation

HRID 596407 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:12](O)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>[Cl-].[Zn+2].[Cl-]>[CH2:25]([C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1]([OH:11])=[CH:2][CH:3]=1)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]

Participants

4

Reactant 2

HCID 70051-NaphtholHCID 82091-Tetradecanol

Product 1

HCID 53733484HCID 53733484, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

In a one liter three-neck flask provided with agitating means were charged and stirred 216 g (1.5 mole) of α-naphthol and 171 g (1.26 mole) of zinc chloride, 278 g (1.26 mole) of tetradecyl alcohol was added dropwise to the flask kept at 160° C. Stirring was continued for 8 hours after the completion of the addition at the same temperature. The reaction product was cooled to room temperature (i.e., 20°-30° C), and then washed with water after the addition of 500 ml of petroleum ether and 500 ml of water with stirring. This washing operation was repeated twice. The petroleum ether layer was separated, which was distilled under a reduced pressure after being dried with anhydrous sodium sulfate. 183 g of 4-tetradecyl-α-naphthol (yield: 42.7%) having boiling range of 188° to 194° C at 0.15 mmHg was obtained.

Workup

  1. customIn a one liter three-neck flask provided with agitating means
  2. additionwere charged
  3. additionwas added dropwise to the flask
  4. customkept at 160° C
  5. additionafter the completion of the addition at the same temperature
  6. washwashed with water
  7. additionafter the addition of 500 ml of petroleum ether and 500 ml of water
  8. stirringwith stirring
  9. customThe petroleum ether layer was separated
  10. distillationwhich was distilled under a reduced pressure
  11. dry with materialafter being dried with anhydrous sodium sulfate

Sources & evidence

ORD record
ord-c11f6eaa7d8b461bbcde09014bde7bcb
Source dataset
uspto-grants-1977_03
Patent number
US04011082

Reaction notes

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