p-Toluenesulfonic acid → 3-Methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl acetate

HRID 1992812Notes

Reaction equation

HRID 1992812 reaction equation
[CH3:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:12][CH3:13])[CH:9]=2)[C:4](=[O:14])[CH:3]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(C1C(=O)C(Cl)=C(Cl)[C:36](=[O:37])[C:35]=1C#N)#N>C(OC(C)C)(=O)C>[C:36]([O:14][C:4]1[C:5]2[C:10](=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2)[CH:11]=[C:2]([CH3:1])[C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:37])[CH3:35]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 685394423-methyl-6-(methyloxy)-2-phenyl-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 685409493-Methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl acetateYield 94%

Reagents, catalysts & solvents 1

HCID 7915Isopropyl AcetateSolvent

Procedure

A round-bottomed flask was charged with 3-methyl-6-(methyloxy)-2-phenyl-3,4-dihydro-1(2H)-naphthalenone (5) (3.8 g, 14.3 mmol), Isopropyl acetate (70 mL), and p-toluene sulfonic acid (1.4 g, 7.14 mmol). The reaction mixture was refluxed for 16 h under N2. Reaction mixture was cooled to room temperature and DDQ (9.74 g, 43 mmol) was introduced to the reaction mixture and refluxed for an additional 3 h. Reaction mixture was concentrated under reduced pressure to afford the crude product. The product was purified by SiO2 column chromatography using hexanes:EtOAc (19:1 to 9:1) as an eluent to afford 4.10 g (94%) of the title compound (6). 1H NMR (400 MHz, CDCl3): δ 7.64 (d, J=12.0 Hz, 1H), 7.55 (br s, 1H), 7.43 and 7.39 (dd, J1=16.0 Hz, J2=8.0 Hz, 2H), 7.38 and 7.34 (m, 1H), 7.26-7.24 (m, 2H), 7.14-7.11 (m, 2H), 3.92 (s, 3H), 2.22 (s, 3H), 2.00 (s, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h under N2
  2. customReaction mixture
  3. temperaturerefluxed for an additional 3 h
  4. customReaction mixture
  5. concentrationwas concentrated under reduced pressure
  6. customto afford the crude product
  7. customThe product was purified by SiO2 column chromatography

Sources & evidence

ORD record
ord-1f3b5af7e20b47778f98b3797627982c
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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