2-Naphthol → 6-tert-butyl-2-naphthol

HRID 1655300Notes

Reaction equation

HRID 1655300 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].[C:12](Cl)([CH3:15])([CH3:14])[CH3:13].[OH-].[Na+]>C(Cl)Cl>[C:12]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[CH:1]=[C:2]([OH:11])[CH:3]=[CH:4]2)([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 86632-NaphtholHCID 10486tert-BUTYL CHLORIDEHCID 14798Sodium Hydroxide

Product 1

HCID 119589826-tert-butyl-2-naphtholYield 14.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 2 L round bottomed flask was charged with freshly fused zinc chloride (45.0 g.); β-naphthol (150.0 g; 1.04 mol) and hexanes (450 ml). The mixture was stirred vigorously while adding t-butyl chloride (150.0 g; 1.62 mol) dropwise over 30 min. When the reaction mixture was gradually heated to reflux, a solution was not obtained. The reaction mixture was cooled to room temperature and 100 ml of CH2Cl2 was added. The reaction mixture was refluxed overnight, cooled and concentrated under vacuum to afford a white solid. The solid was refluxed with 1800 ml of 10% NaOH, filtered, and allowed to cool. The white sodium salt which precipitated was collected by filtration. The solid collected by filtration was stirred with excess 5.0M HCl and the resulting phenol was collected by filtration and washed with 2 L of water. Recrystallization from heptane afforded 30.67 g of the subtitle compound as a white solid.

Workup

  1. temperatureWhen the reaction mixture was gradually heated
  2. temperatureto reflux
  3. customa solution was not obtained
  4. temperatureThe reaction mixture was refluxed overnight
  5. temperaturecooled
  6. concentrationconcentrated under vacuum
  7. customto afford a white solid
  8. filtrationfiltered
  9. temperatureto cool
  10. customThe white sodium salt which precipitated
  11. filtrationwas collected by filtration
  12. filtrationThe solid collected by filtration
  13. stirringwas stirred with excess 5.0M HCl
  14. filtrationthe resulting phenol was collected by filtration
  15. washwashed with 2 L of water
  16. customRecrystallization from heptane

Sources & evidence

ORD record
ord-14117c1f8fd54dda976673cc593a0af1
Source dataset
uspto-grants-1993_10
Patent number
US05250539

Reaction notes

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