Ethyl Acetate → 6-Benzyloxy-2-(4-fluoro-phenyl)-naphthalen-1-ol

HRID 1513865Notes

Reaction equation

HRID 1513865 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([O:19]S(C)(=O)=O)=[C:14]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(OCC)(=O)C>C1COCC1.CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([OH:19])=[C:14]([C:24]1[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=1)[CH:13]=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 86626527Methanesulfonic acid 6-benzyloxy-2-(4-fluoro-phenyl)-naphthalen-1-yl ester

Product 1

HCID 670047546-Benzyloxy-2-(4-fluoro-phenyl)-naphthalen-1-olYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Dissolve methanesulfonic acid 6-benzyloxy-2-(4-fluoro-phenyl)-naphthalen-1-yl ester (5.2 g, 12.3 mmol) in 5M sodium hydroxide (12 mL, 60 mmol), THF (86 mL) and MeOH (86 mL). Heat to 50° C. for 1 hour. Cool and add ethyl acetate (100 mL). Wash the organic layer with 1N HCl, saturated sodium bicarbonate solution and brine. Dry with magnesium sulfate and concentrate in vacuo to obtain 3.4 g (89%) of 6-benzyloxy-2-(4-fluoro-phenyl)-naphthalen-1-ol.

Workup

  1. temperatureCool
  2. washWash the organic layer with 1N HCl, saturated sodium bicarbonate solution and brine
  3. dry with materialDry with magnesium sulfate
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-9dec469626de4aaa8d2d7ef49b30542a
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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