Dichloromethane → 5,6,7,8-Tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl ethyl ketone

HRID 1614882Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To 5,6,7,8-tetrahydro-2-hydroxy-5,5,8,8-tetramethylnaphthalene (204 mg, 1.00 mmol) were added anhydrous dichloromethane (1 mL), aluminum chloride (148 mg, 1.12 mmol), and propionyl chloride (101.7 mg, 1.10 mmol) followed by stirring at 60° C. for 16 hours. The reaction solution was poured into cold water and extracted by ethyl acetate. The organic layer was washed by water, a saturated sodium hydrogen carbonate aq. solution, and a saturated saline solution, dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using hexane/ethyl acetate (20/1) as an elution solvent. The yield was 117 mg (45%).

Workup

extractionextracted by ethyl acetate
washThe organic layer was washed by water
dry with materiala saturated sodium hydrogen carbonate aq. solution, and a saturated saline solution, dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-2ccb158dc8244890a8d5a71e3e4e8d4b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765719B2

Reaction notes

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