Hydrochloric Acid → HCID 11233100, compound

HRID 397585Notes

Reaction equation

HRID 397585 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([OH:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>CCCCCC.C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:24]2[CH:25]=[CH:26][C:21]([OH:27])=[CH:22][CH:23]=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 996Phenol2×HCID 6451240Aluminum(III) ChlorideHCID 11242517HCID 11242517, compound

Product 1

HCID 11233100HCID 11233100, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8058HexaneSolvent

Procedure

A solution of compound (4-methoxyphenyl)-naphth-1-yl-carbinol of formula II (3.0 gm, 0.011 mol) and phenol (5.4 gm, 0.057 mol) in a mixture of anhydrous benzene and anhydrous hexane (40.0 ml), 1:1) was gradually added to a mixture of phenol (1.5 gm, 0.061 mol) and anhydrous aluminum chloride (1.5 gm, 0.011 mol) at 0° C. under stirring. After the addition was over, the stirring was continued at room temperature for 3 hrs, the reaction was decomposed by adding crushed ice with conc. HCl (0.5 ml) and extracted with ethyl acetate. The organic layer was washed with water, 5% NaOH, dried over sodium sulphate and concentrated to give an oil which was chromatographed over silica gel to yield the title compound of formula I. Yield 2.3 gm (59.3%).

Workup

  1. additionAfter the addition
  2. additionby adding
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, 5% NaOH
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customto give an oil which
  8. customwas chromatographed over silica gel

Sources & evidence

ORD record
ord-b7f16a322d654cf99d3e4e777e03403d
Source dataset
uspto-grants-2003_08
Patent number
US06610705B1

Reaction notes

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