Ethyl 4,4-dibutyl-1-hydroxy-3-oxo-3,4-dihydro-2-naphthalenecarboxylate → 1,1-dibutyl-4-hydroxy-2(1H)-naphthalenone

HRID 494454Notes

Reaction equation

[CH2:1]([C:5]1([CH2:22][CH2:23][CH2:24][CH3:25])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7](C(OCC)=O)[C:6]1=[O:21])[CH2:2][CH2:3][CH3:4]>O1CCOCC1.Cl>[CH2:1]([C:5]1([CH2:22][CH2:23][CH2:24][CH3:25])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[CH:7][C:6]1=[O:21])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of the product of Example 4F (200 mg, 0.58 mmol) in dioxane (3 mL) and 10% HCl solution (10 mL) was stirred at 100° C. for 5 hours, cooled to 25° C. and extracted with dichloromethane (3×). The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo. The residue was recrystallized from hexanes to give the title compound (140 mg, 88%). 1H NMR (300 MHz, DMSO-d6): δ 11.72, 11.46 (s, 1 H), 7.92 (m, 1 H), 7.61 (m, 1 H), 7.37 (m, 2 H), 5.81, 5.64 (two s, 1 H), 1.99 (m, 4 H), 1.05 (m, 4 H), 0.82 (m, 2 H), 0.67 (t, J=6.99 Hz, 6 H), 0.44 (m, 2 H).

Workup

extractionextracted with dichloromethane (3×)
dry with materialThe combined organic layers were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was recrystallized from hexanes

Sources & evidence

ORD record: ord-b6dbe1e822d648d186018b4a231effb7
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538105B2

Reaction notes

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