Acetic Acid → 1-benzyl-7-methoxy-3,4-dihydronaphthalen-2(1H)-one

HRID 2170520Notes

Reaction equation

HRID 2170520 reaction equation
[Br-].[CH2:2]([CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=2)[CH2:12][CH2:11][C:10]1=[N+]1CCCC1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CC(O)=[O:28]>C(Cl)Cl.O.CO>[CH2:2]([CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=2)[CH2:12][CH2:11][C:10]1=[O:28])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 71008563HCID 71008563, compound

Product 1

HCID 214101101-benzyl-7-methoxy-3,4-dihydronaphthalen-2(1H)-oneYield 53%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(1-benzyl-7-methoxy-3,4-dihydro-1H-naphthalen-2-ylidene)-pyrrolidinium bromide and AcOH (300 mL) in DCM (500 mL), H2O (3000 mL) and MeOH (500 mL) was stirred at reflux for 10 hrs. The aqueous layer was washed with DCM (1000 mL), and the combined organic layers were washed with water, dried over Na2SO4 and concentrated to give crude product, purified by silica gel chromatography to give 1-benzyl-7-methoxy-3,4-dihydro-1H-naphthalen-2-one (195 g, yield 53%) as yellow solid.

Workup

  1. temperatureat reflux for 10 hrs
  2. washThe aqueous layer was washed with DCM (1000 mL)
  3. washthe combined organic layers were washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give crude product
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-7813a34fb4ce4b0380175038a4dd471f
Source dataset
uspto-grants-2015_06
Patent number
US09051280B2

Reaction notes

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