Hydrochloric Acid → 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 484374

反応式

HRID 484374 の反応式
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][C:9]1([CH3:16])[CH2:13][CH2:12][C:11]([CH3:15])([CH3:14])O1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>CCCCCCC>[CH3:8][C:9]1([CH3:16])[CH2:13][CH2:12][C:11]([CH3:15])([CH3:14])[C:5]2[CH:6]=[C:1]([OH:7])[CH:2]=[CH:3][C:4]1=2

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 270102,2,5,5-TetramethyltetrahydrofuranHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 2687865,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol

試薬・触媒・溶媒 1

HCID 8900Heptane溶媒

実験手順

To a stirred solution of 13.2 g (0.1403 mol) of phenol and 12.8 g (0.0998 mol) of 2,2,5,5-tetramethyltetrahydrofuran in 50 ml of heptane was added 13.1 g (0.0982 mol) of aluminum chloride in small portions. After the addition was complete the mixture was stirred at room temperature for 2.5 hours, at reflux for 2 hours and then at room temperature for a further 16 hours. The reaction mixture was then treated with 100 ml of 3N HCl and stirred for 0.5 hours. The mixture was filtered and the residue washed with water and dried in-vacuo to give crude product. The organic layer was separated from the filtrate and the aqueous layer extracted with 3×75 ml of ether. The organic layers were combined and washed with saturated NaCl solution, dried (MgSO4) and then concentrated in-vacuo to give further crude product. The crude product was recrystallized from hexanes to give the title compound as pale brown crystals. PMR (CDCl3): δ 1.26 (6 H, s), 1.28 (6H, s), 1.67 (4H, s), 5.08 (1H, broad s), 6.68 (1H, dd, J~8.7 Hz, 2.7 Hz), 6.82 (1H, d, J~2.7 Hz), 7.16 (1H, d, J~8.7 Hz).

後処理

  1. additionAfter the addition
  2. temperatureat reflux for 2 hours
  3. waitat room temperature for a further 16 hours
  4. stirringstirred for 0.5 hours
  5. filtrationThe mixture was filtered
  6. washthe residue washed with water
  7. customdried in-vacuo
  8. customto give crude product
  9. customThe organic layer was separated from the filtrate
  10. extractionthe aqueous layer extracted with 3×75 ml of ether
  11. washwashed with saturated NaCl solution
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated in-vacuo
  14. customto give further crude product
  15. customThe crude product was recrystallized from hexanes

出典と根拠

ORDレコード
ord-3b28345b2736485ab4609307efc89ec0
出典データセット
uspto-grants-1993_07
特許番号
US05231113

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