3-Methyl-6-(methyloxy)-1-{[(methyloxy)methyl]oxy}-2-phenylnaphthalene → 6-Methoxy-3-methyl-2-phenyl-1-naphthol

HRID 1992828Notes

Reaction equation

HRID 1992828 reaction equation
[CH3:1][C:2]1[C:3]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:4]([O:14]COC)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2>Cl.O1CCOCC1>[CH3:13][O:12][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[C:4]([OH:14])=[C:3]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:2]([CH3:1])=[CH:11]2

Participants

4

Reactant 1

HCID 685363903-Methyl-6-(methyloxy)-1-{[(methyloxy)methyl]oxy}-2-phenylnaphthalene

Product 1

HCID 685363886-Methoxy-3-methyl-2-phenyl-1-naphtholYield 100%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

6-methoxy-1-(methoxymethoxy)-3-methyl-2-phenylnaphthalene (15) (500 mg, 1.62 mmol, 1 equiv) was dissolved in 4 N HCl in dioxane (5 mL) and the mixture was stirred at RT for 1 h. The reaction was then concentrated to dryness to provide 7 (428 mg, 100%) as a tan oil. 1H NMR (400 MHz, DMSO-d6): δ 8.59 (s, 1H), 8.04 (m, 1H), 7.38 (m, 3H), 7.21 (m, 4H), 7.03 (m, 1H), 3.84 (s, 3H), 2.06 (m, 3H). LRMS m/z 265.1 (M+H)+.

Workup

  1. concentrationThe reaction was then concentrated to dryness

Sources & evidence

ORD record
ord-a29d7ad658194bf8ba6eeb764805f367
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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