Hydrogen Bromide → 1-Hydroxy-5-phenoxynaphthalene

HRID 2288907Notes

Reaction equation

HRID 2288907 reaction equation
C[O:2][C:3]1[C:12]2[C:7](=[C:8]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.Br>C(O)(=O)C>[OH:2][C:3]1[C:12]2[C:7](=[C:8]([O:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 187020411-Methoxy-5-phenoxynaphthalene

Product 1

HCID 187020401-Hydroxy-5-phenoxynaphthaleneYield 60.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
97.5 °C

Procedure

Into 50 mL of glacial acetic acid, 3.7 g of 1-methoxy-5-phenoxynaphthalene prepared as above, followed by 20 mL of 40% aqueous hydrogen bromide was stirred. The mixture was heated at 95-100° C. for 16 hours. The solvent was removed under vacuum, and the residue was redissolved in ethyl acetate and washed three times with brine. The organic layer was dried over magnesium sulfate and filtered. After removing solvent, the residue was chromatographed over silica gel with a gradient elution of 0 to 30% ethyl acetate in hexane, providing 2.10 g (59%) of 1-hydroxy-5-phenoxynaphthalene.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue was redissolved in ethyl acetate
  3. washwashed three times with brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customAfter removing solvent
  7. customthe residue was chromatographed over silica gel with a gradient elution of 0 to 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d1b49b4548f74fc59f1de55bc3c97665
Source dataset
uspto-grants-2000_07
Patent number
US06090850

Reaction notes

Loading…