Hydrochloric Acid → 3-Phenyl-1,2-dihydronaphthalene

HRID 397139

Reaction equation

HRID 397139 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=O.[C:12]1([Mg]Cl)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCCCCCCCCCCCC.Cl>C1COCC1.C1(C)C=CC=CC=1>[C:12]1([C:2]2[CH2:3][CH2:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12388TridecaneHCID 682662-Tetralone2×HCID 178478979HCID 178478979, compound

Product 1

HCID 2466083-Phenyl-1,2-dihydronaphthaleneYield 29%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1.32 mL (10.0 mmol) 2-tetralone in 5 mL of THF was added to a solution of 5.77 mL (12.0 mmol) 2.08 M phenylmagnesium chloride in THF at 0° C. The mixture was allowed to warm to room temperature, and was then stirred for an additional 1 hour. Tridecane (1.22 mL; 5.00 mmol; internal GC standard) was added, the mixture was cooled to 0°, 10 mL of 6N HCl was added. The mixture was heated to 65° and vigorously stirred for 4 hours. The mixture was then cooled to room temperature and diluted with toluene. GC analysis of the organic phase showed the presence of 2.9 mmol 2-phenyl-3,4-dihydronaphthalene (29% yield on 2-tetralone) and 4.6 mmol 2-tetralone (46% recovery). No benzylic alcohol intermediate from addition of the arylmagnesium reagent to the ketone was detected, indicating that its dehydration to the vinylaromatic had been completed by the warm acid treatment.

Workup

  1. temperaturethe mixture was cooled to 0°
  2. temperatureThe mixture was heated to 65°
  3. stirringvigorously stirred for 4 hours
  4. temperatureThe mixture was then cooled to room temperature

Sources & evidence

ORD record
ord-41c7e5b7fbac41558bb3cd7ee1c1d25c
Source dataset
uspto-grants-2003_08
Patent number
US06608212B1

Linked notes

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