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

HRID 397139

반응식

HRID 397139 반응식
[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

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 12388TridecaneHCID 682662-Tetralone2회HCID 178478979HCID 178478979, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-41c7e5b7fbac41558bb3cd7ee1c1d25c
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06608212B1

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