Hydrochloric Acid → HCID 68538747, compound

HRID 1992912Notes

Reaction equation

HRID 1992912 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH2:22][CH2:23][CH3:24])[C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:9]2[O:12]COC)=[CH:4][C:3]=1[O:25][CH3:26].Cl>O1CCOCC1>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH2:22][CH2:23][CH3:24])[C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:9]2[OH:12])=[CH:4][C:3]=1[O:25][CH3:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68537241HCID 68537241, compound

Product 1

HCID 68538747HCID 68538747, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

7-Fluoro-6-(methyloxy)-1-{[(methyloxy)methyl]oxy}-2-phenyl-3-propyl naphthalene (136) (0.48 g, 1.34 mmol) was treated with 4 M HCl in dioxane at room temperature to give 0.42 g (˜100%) of the title compound (137) as a light yellow viscous oil. 1H NMR (400 MHz, CDCl3): δ 0.79 (t, J=7.4 Hz, 3H), 1.40-1.60 (m, 2H), 2.44 (t, J=7.8 Hz, 2H), 4.00 (s, 3H), 5.13 (s, 1H), 7.13 (d, J=8.2 Hz, 1H), 7.21 (s, 1H), 7.30-7.36 (m, 2H), 7.42-7.49 (m, 1H), 7.50-7.56 (m, 2H), 7.79 (d, J=12.5 Hz, 1H). LCMS (ESI): m/z 311 (M+H)+, m/z 309 (M−H)−.

Sources & evidence

ORD record
ord-224c46d2cef44ed6a33cc34973f321c1
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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