Sodium Methoxide → 6-Methoxy-3-methyl-2-phenyl-1-naphthol

HRID 1992813Notes

Reaction equation

HRID 1992813 reaction equation
C([O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[CH:8]=[C:7]([CH3:17])[C:6]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=O)C.C[O-].[Na+]>C1COCC1.CO>[CH3:16][O:15][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[C:5]([OH:4])=[C:6]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:7]([CH3:17])=[CH:8]2

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 685409493-Methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl acetate

Product 1

HCID 685363886-Methoxy-3-methyl-2-phenyl-1-naphtholYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl acetate (6) (4.00 g, 13.1 mmol) in THF and MeOH (200 mL, 1:1) was added sodium methoxide (26 mL, 0.5 M solution in MeOH) at room temperature. The reaction mixture was stirred for 3 h under N2. The reaction mixture was concentrated under reduced pressure to afford the crude product, which was purified by SiO2 column chromatography to afford 3.4 g (99%) of compound 7 as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.10 (d, J=8.0 Hz, 1H), 7.54 (dd, J1=12.0 Hz, J2=8.0 Hz, 2H), 7.45 (dd, J1=8.0 Hz, J2=8.0 Hz, 1H), 7.36 (d, J1=4.0 Hz, 2H), 7.23 (s, 1H), 7.10 and 7.08 (dd, J1=8.0 Hz, J2=4.0 Hz, 1H), 7.05 (d, J1=4.0 Hz, 1H), 5.21 (s, 1H), 3.93 (s, 3H), 2.18 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto afford the crude product, which
  3. customwas purified by SiO2 column chromatography

Sources & evidence

ORD record
ord-1c5a365f66ec4558bc69ac9c90dcf394
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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