3-Methoxyphenol → 7-Methoxy-1,2,3,4,4a,9b-hexahydro-dibenzofuran

HRID 237829

Reaction equation

HRID 237829 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[CH:10]1[CH2:15][CH2:14][CH:13]=[CH:12][CH:11]=1>C(Cl)Cl.C(S([O-])(=O)=O)(F)(F)F.[Ag+]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]3[O:9][C:5]=2[CH:4]=1.[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C:10]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[O:9][C:5]=2[CH:4]=1

Participants

6

Reactant 2

HCID 90073-MethoxyphenolHCID 116051,3-Cyclohexadiene

Product 2

HCID 685259167-Methoxy-1,2,3,4,4a,9b-hexahydro-dibenzofuranHCID 685276477-Methoxy-1,2,3,4-tetrahydro-dibenzofuran

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
40 °C

Procedure

A solution of AuCl3 (0.303 g, 1.0 mmol) and AgOTf (0.770 g, 3.0 mmol) was stirred in anhydrous CH2Cl2 (150 mL) for 2 hours. 3-methoxy-phenol (2.48 g, 20 mmol) in CH2Cl2 (25 mL) was added, followed by addition of cyclohexadiene in CH2Cl2 (25 mL) at 40° C. over two hours. The reaction mixture was stirred at 40° C. overnight. The reaction mixture was passed through a silica gel plug. The filtrate was concentrated. The residue was purified by silica gel chromatography (5-30% CH2Cl2/heptane) to give 0.393 g of the title compound and 0.67 g of 7-methoxy-1,2,3,4-tetrahydro-dibenzofuran.

Workup

  1. concentrationThe filtrate was concentrated
  2. customThe residue was purified by silica gel chromatography (5-30% CH2Cl2/heptane)

Sources & evidence

ORD record
ord-879e9f50f5df4bb7858c6c8777c461c0
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Linked notes

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