Hydrochloric Acid → (1r)-1-(3,3-Dimethylbutyl)-4-hydroxy-1-methylnaphthalen-2(1h)-one

HRID 494590Notes

Reaction equation

HRID 494590 reaction equation
[CH3:1][C:2]([CH3:24])([CH3:23])[CH2:3][CH2:4][C@:5]1([CH3:22])[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].Cl>O1CCOCC1>[CH3:1][C:2]([CH3:24])([CH3:23])[CH2:3][CH2:4][C@:5]1([CH3:22])[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]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54740013Ethyl(4R)-4-(3,3-dimethylbutyl)-1-hydroxy-4-methyl-3-oxo-3,4-dihydronaphthalene-2-carboxylate

Product 1

HCID 25260417(1r)-1-(3,3-Dimethylbutyl)-4-hydroxy-1-methylnaphthalen-2(1h)-oneYield 78.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of Example 49C (2.65 g, 8.02 mmol) in 1,4-dioxane (25 mL) was treated with aqueous 1 N hydrochloric acid solution (25 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 dried to give 1.62 g (61%) of the title compound. 1H NMR (300 MHz, CDCl3): δ ppm 0.43 (m, 0.5H) 0.83 (m, 10H) 1.06 (m, 0.5H) 1.51 (s, 1.5H) 1.56 (s, 1.5H) 1.83 (m, 1H) 2.02 (m, 0.5H) 2.26 (m, 0.5H) 3.74 (s, 1H) 6.09 (s, 0.5H) 7.51 (m, 3H) 8.10 (td, J=7.81, 1.29 Hz, 1H); MS (ESI−) m/z 257 (M−H)−.

Workup

  1. temperaturerefluxed for 3 hours
  2. custompartitioned between ethyl acetate and water
  3. washThe ethyl acetate layer was washed with water and brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated in hot hexane
  8. customdried

Sources & evidence

ORD record
ord-e77b8d628f584b5c995b2c07c8cdb47f
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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