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

HRID 397139

反応式

HRID 397139 の反応式
[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

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 12388TridecaneHCID 682662-Tetralone2 回HCID 178478979HCID 178478979、化合物

生成物 1

HCID 2466083-Phenyl-1,2-dihydronaphthalene収率 29%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-41c7e5b7fbac41558bb3cd7ee1c1d25c
出典データセット
uspto-grants-2003_08
特許番号
US06608212B1

関連ノート

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