Diethyl Ether → 1-Phenylnaphthalen-2-ol

HRID 563455Notes

Reaction equation

HRID 563455 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.B(Br)(Br)Br.C(OCC)C>C(Cl)Cl>[C:13]1([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:11]=[CH:12][C:3]=2[OH:2])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 25134Boron tribromideHCID 113222662-Methoxy-1-phenylnaphthalene

Product 1

HCID 112182821-Phenylnaphthalen-2-olYield 81.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In methylene chloride (300 mL), dissolved was 2-methoxy-1-phenylnaphthalene (13.0 g, 55.5 mmol), and 670 mL of boron tribromide solution (1 M in methylene chloride) was added dropwise thereto at −78° C. Reaction was carried out for 3 hours while slowly raising the temperature to ambient temperature. When the reaction was completed, mixture of ice (150 g) and diethyl ether (250 mL) was added thereto. After isolating the organic layer, the aqueous layer was extracted with diethyl ether. The combined organic layer was dried over magnesium sulfate, and evaporated to remove the volatiles. The residue was purified via silica gel column chromatography by using mixed solvent of hexane and methylene chloride to obtain 1-phenylnaphthalen-2-ol (10.0 g, yield: 81.8%) as white solid.

Workup

  1. additionwas added dropwise
  2. customat −78° C
  3. customReaction
  4. additionwas added
  5. customAfter isolating the organic layer
  6. extractionthe aqueous layer was extracted with diethyl ether
  7. dry with materialThe combined organic layer was dried over magnesium sulfate
  8. customevaporated
  9. customto remove the volatiles
  10. customThe residue was purified via silica gel column chromatography
  11. additionby using mixed solvent of hexane and methylene chloride

Sources & evidence

ORD record
ord-b8ea0ded6ffb4822898b5ea482c2e34f
Source dataset
uspto-grants-2011_11
Patent number
US08067511B2

Reaction notes

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