tert-Butyl hydroperoxide → 4-Allyl-3-methoxy-4-methylnaphthalen-1(4h)-one

HRID 2224947Notes

Reaction equation

HRID 2224947 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:14][CH:15]=[CH2:16])([CH3:13])[C:5]2[C:10]([CH2:11][CH:12]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:18].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(OO)(C)(C)C>C1C=CC=CC=1>[CH2:14]([C:4]1([CH3:13])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:11](=[O:18])[CH:12]=[C:3]1[O:2][CH3:1])[CH:15]=[CH2:16]

Participants

5

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 2724130Cornforth reagentHCID 688737961-Allyl-1-methyl-1,4-dihydronaphthalen-2-yl methyl ether

Product 1

HCID 688739624-Allyl-3-methoxy-4-methylnaphthalen-1(4h)-oneYield 25%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of Example 123B (7.72 g, 36.1 mmol) in benzene (400 mL) was added celite (15 g), pyridinium dichromate (54.3 g, 144.3 mmol) and tert-butylhydroperoxide (70% in water) (19.9 mL, 144.3 mmol). The resultant solution was stirred at room temperature for 1.25 hours, followed by filtering the solution through a plug of celite (20 g) which was rinsed with benzene (100 mL). The combined filtrate was concentrated in vacuo, and the resultant residue was purified by column chromatography employing 70-230 mesh silica gel eluting with a mixture of 20% ethyl acetate in hexane followed by 50% ethyl acetate in hexane to provide the title compound as a light yellow oil (2.05 g, 25%). 1H NMR (300 MHz, DMSO-d6): δ 1.53 (s, 3 H), 2.77 m, 2 H), 3.82 (s, 3 H), 4.75 m, 2 H), 5.02 (m, 1H), 5.84 (s, 1 H), 7.42 m, 1 H), 7.65 (dt, J=8.1, 1.5 Hz, 1 H), 7.76 (d, J=8.1 Hz, 1 H), 7.96 (dd, J=7.7, 1.5 Hz, 1 H).

Workup

  1. filtrationby filtering the solution through a plug of celite (20 g) which
  2. washwas rinsed with benzene (100 mL)
  3. concentrationThe combined filtrate was concentrated in vacuo
  4. customthe resultant residue was purified by column chromatography
  5. additionwith a mixture of 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-36c62cfcf6d04b0d8172d4ea434e3908
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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