Sulfuric Acid → Ethyl 1-hydroxy-3-oxo-4,4-dipropyl-3,4-dihydro-2-naphthalenecarboxylate

HRID 2224759Notes

Reaction equation

[C:1]1([C:7]([CH2:24][CH2:25][CH3:26])([CH2:21][CH2:22][CH3:23])[C:8]([CH:10]([C:16](OCC)=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O>O>[OH:17][C:16]1[C:6]2[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=2)[C:7]([CH2:24][CH2:25][CH3:26])([CH2:21][CH2:22][CH3:23])[C:8](=[O:9])[C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

Conditions

Temperature: 25 °C

Procedure

The product of Example 1E (4.51 g, 12.4 mmol) was treated with concentrated sulfuric acid (25 mL) and stirred at 25° C. for 3 hours. The mixture was then poured into a mixture of ice and water (500 mL) and stirred until all the ice melted. The mixture was extracted with ethyl acetate (2×). The combined organic layers were washed with water and saturated sodium chloride solution, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was chromatographed on silica gel, eluting with methyl t-butyl ether in hexane to afford the title compound (1.73 g, 44%). 1H NMR (300 MHz, CDCl3): δ 15.15 (d, J=13.24 Hz, 1 H), 8.18 (m, 1 H), 7.59 (m, 1 H), 7.40 (m, 2 H), 4.47 (m, 2 H), 2.25 (m, 2 H), 1.91 (m, 1 H), 1.70 (m, 1 H), 1.47 (q, J=7.23 Hz, 3 H), 1.25 (m, 1 H), 0.93 (m, 2 H), 0.67 (m, 7 H).

Workup

extractionThe mixture was extracted with ethyl acetate (2×)
washThe combined organic layers were washed with water and saturated sodium chloride solution
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was chromatographed on silica gel
washeluting with methyl t-butyl ether in hexane

Sources & evidence

ORD record: ord-c422eb42d0c84458a33a63476fd00a4a
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378414B2

Reaction notes

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