Hydrochloric Acid → 1-(5,5-Dimethylhexyl)-4-hydroxy-1-methylnaphthalen-2(1h)-one

HRID 494538Notes

Reaction equation

[CH3:1][C:2]([CH3:26])([CH3:25])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1([CH3:24])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([OH:17])=[C:9](C(OCC)=O)[C:8]1=[O:23].Cl>O1CCOCC1>[CH3:1][C:2]([CH3:26])([CH3:25])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1([CH3:24])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([OH:17])=[CH:9][C:8]1=[O:23]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of Example 35F (1.84 g, 5.13 mmol) in 1,4-dioxane (20 mL) was treated with aqueous 1N hydrochloric acid solution (20 mL) and refluxed for 3 hours. The mixture was cooled to 25° C. and partitioned between ethyl acetate and water. The ethyl acetate layer was washed with water and brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was triturated in hot hexane and filtered. The precipitate was dried to give the title compound (1.06 g, 72%). 1H NMR (300 MHz, CDCl3) δ ppm 0.57 (m, 1 H) 0.75 (s, 4.5 H) 0.80 (s, 4.5 H) 1.02 (m, 5 H) 1.51 (s, 1.5 H) 1.56 (s, 1.5 H) 1.84 (m, 1 H) 2.04 (m, 0.5 H) 2.25 (m, 0.5 H) 3.74 (s, 0.5 H) 3.75 (s, 0.5 H) 6.00 (s, 0.5 H) 7.51 (m, 3 H) 8.09 (m, 1 H). (ESI+) m/z 287 (M+H)+.

Workup

temperaturerefluxed for 3 hours
custompartitioned between ethyl acetate and water
washThe ethyl acetate layer was washed with water and brine
dry with materialdried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was triturated in hot hexane
filtrationfiltered
customThe precipitate was dried

Sources & evidence

ORD record: ord-b29fe7f8ff4245e68e439826180e3f91
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538105B2

Reaction notes

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