Hydrochloric Acid → 7-(Benzyloxy)-4-methyl-1,2-dihydronaphthalene

HRID 243818Notes

Reaction equation

HRID 243818 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=O)[CH2:14][CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O1CCC[CH2:22]1>C[Mg]Br>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16]([C:15]([CH3:22])=[CH:14][CH2:13][CH2:12]2)=[CH:17][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 106822416-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 231216717-(Benzyloxy)-4-methyl-1,2-dihydronaphthalene

Reagents, catalysts & solvents 1

HCID 178418573HCID 178418573, compoundSolvent

Procedure

To a solution of the obtained 6-(benzyloxy)-3,4-dihydronaphtalen-1(2H)-one (34.5 g) in tetrahydrofuran (300 mL), methyl magnesium bromide (3M diethyl ether solution, 55 mL) was added at 0° C., followed by stirring at room temperature for 1 hour. The reaction mixture was cooled to 0° C. and poured into ice-saturated aqueous ammonium chloride solution. After adding 2N hydrochloric acid, the mixture was stirred at room temperature for 3 hours. Then, the resultant was extracted with ethyl acetate and the organic layer was successively washed with water and brine, dried and concentrated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to thereby give the title compound (24.8 g) having the following physical properties.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. additionpoured into ice-saturated aqueous ammonium chloride solution
  3. stirringthe mixture was stirred at room temperature for 3 hours
  4. extractionThen, the resultant was extracted with ethyl acetate
  5. washthe organic layer was successively washed with water and brine
  6. customdried
  7. concentrationconcentrated
  8. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-8003e202c2464e00a1cdd6a6fbb8bf3c
Source dataset
uspto-grants-2014_02
Patent number
US08653305B2

Reaction notes

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