Boron tribromide → 6-Hydroxy-7-methyl-1,2,3,4-tetrahydronaphthalen-1-one

HRID 1386407

反応式

HRID 1386407 の反応式
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[C:9](=[O:14])[CH2:8][CH2:7][CH2:6]2.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[C:9](=[O:14])[CH2:8][CH2:7][CH2:6]2

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 113559636-methoxy-7-methyl-3,4-dihydronaphthalen-1(2H)-one

生成物 1

HCID 186264826-Hydroxy-7-methyl-1,2,3,4-tetrahydronaphthalen-1-one収率 80.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A solution of 2.79 g (14.7 mmol) of 6-methoxy-7-methyl-1,2,3,4-tetrahydro-1-naphthalenone in 150 mL of CH2Cl2 was cooled in ice and treated with 20 mL (0.22 mol) of BBr3. After stirring at 0° C. for 0.5 hour, the solution was stirred at room temperature overnight. The solution was poured into ice water and extracted with Et2O. The Et2O was extracted twice with 5% NaOH and the NaOH washed with Et2O. The NaOH solution was acidified to the Congo Red end point with dilute HCl, then extracted with Et2O. The Et2O was washed with saturated NaCl and dried over MgSO4. Removal of the solvent under reduced pressure left the crude product. This was taken up in acetone and treated with charcoal. Filtering through Celite and removal of the solvent under reduced pressure left 2.08 g (80.6% yield) of the product as a brown solid. The structure was confirmed by NMR and mass spectroscopy. MS m/z 177 (M+H+).

後処理

  1. stirringthe solution was stirred at room temperature overnight
  2. extractionextracted with Et2O
  3. extractionThe Et2O was extracted twice with 5% NaOH
  4. washthe NaOH washed with Et2O
  5. extractionextracted with Et2O
  6. washThe Et2O was washed with saturated NaCl
  7. dry with materialdried over MgSO4
  8. customRemoval of the solvent under reduced pressure
  9. waitleft the crude product
  10. additiontreated with charcoal
  11. filtrationFiltering through Celite and removal of the solvent under reduced pressure

出典と根拠

ORDレコード
ord-16d086381411490bba836103bee8091d
出典データセット
uspto-grants-2001_07
特許番号
US06265422B1

関連ノート

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