Hydrochloric Acid → Phenol, 4-[(4-methoxyphenyl)-1-naphthalenylmethyl]-2-methyl-

HRID 397586Notes

Reaction equation

HRID 397586 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)O)=[CH:5][CH:4]=1.[C:21]1([CH3:28])[C:26]([OH:27])=[CH:25][CH:24]=[CH:23][CH:22]=1.[Al+3].[Cl-].[Cl-].[Cl-].Cl>CCCCC.C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:23]2[CH:24]=[CH:25][C:26]([OH:27])=[C:21]([CH3:28])[CH:22]=2)[C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 335O-CresolHCID 6451240Aluminum(III) ChlorideHCID 11242517HCID 11242517, compound

Product 1

HCID 11256744Phenol, 4-[(4-methoxyphenyl)-1-naphthalenylmethyl]-2-methyl-

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8003PentaneSolvent

Procedure

To a stirred solution of (4-methoxyphenyl)-naphth-1-yl carbinol of formula II (5.0 gm, 0.018 mol )and o-cresol (2.4 ml, 0.022 mol) in a mixture of anhydrous benzene, anhydrous pentane (50 ml, 1:1), and AlCl3 (2.5 gm) was gradually added, after addition stirring was continued for 5-6 hrs at 0-4° C. The reaction mixture was decomposed by adding crushed ice with conc. HCl (0.5 ml) and extracted with ethyl acetate. The organic layer was washed successively with water, dried over Na2SO4 and concentrated to give an oil, which was chromatographed over silica gel using benzene-hexane as the eluent to give the title compound of formula III, yield 4.5 gm (67.16%).

Workup

  1. additionwas gradually added
  2. additionafter addition
  3. additionby adding
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed successively with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto give an oil, which
  9. customwas chromatographed over silica gel

Sources & evidence

ORD record
ord-4e650ad0f7c94a95b71a5b3b38da3d41
Source dataset
uspto-grants-2003_08
Patent number
US06610705B1

Reaction notes

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