Hydrochloric Acid → HCID 68537270, compound

HRID 1992866Notes

Reaction equation

HRID 1992866 reaction equation
[CH3:1][CH:2]([C:4]1[C:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:6]([O:16]COC)[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=2)[CH3:3].Cl>O1CCOCC1.O.[Cl-].[Na+].O>[CH3:3][CH:2]([C:4]1[C:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:6]([OH:16])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=2)[CH3:1]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 68539388HCID 68539388, compound

Product 1

HCID 68537270HCID 68537270, compoundYield 99.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

3-(1-Methylethyl)-6-(methyloxy)-1-{[(methyloxy)methyl]oxy}-2-phenyl naphthalene (71) (0.42 g, 1.24 mmol) was dissolved in dioxane (8 mL). 4 M HCl in dioxane (8 mL) was added and the reaction mixture was stirred at room temperature for 30 min. The mixture was diluted with water (25 mL) and brine (25 mL) and extracted with EtOAc (3×50 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a light yellow oil. The crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (20:1) to give 0.36 g (98%) of the title compound (72) as a white solid. 1H NMR (400 MHz, CDCl3): δ 1.16 (d, J=6.8 Hz, 6H), 2.79 (sept, J=6.8 Hz, 1H), 3.93 (s, 3H), 5.08 (s, 1H), 7.05-7.12 (m, 2H), 7.30 (s, 1H), 7.32-7.38 (m, 2H), 7.42-7.50 (m, 1H), 7.50-7.58 (m, 2H), 8.07 (d, J=9.0 Hz, 1H). LCMS (APCI): m/z 293 (M+H)+.

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customto give the crude product as a light yellow oil
  7. customThe crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (20:1)

Sources & evidence

ORD record
ord-6db98b2e20b54d01a3ab8564f16b018a
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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