Epibromohydrin → (7-Nitro-2,3-dihydro-1,4-benzodioxin-2-yl)methanol

HRID 9726

反応式

HRID 9726 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([OH:11])[C:7](=[CH:9][CH:10]=1)[OH:8])([O-:3])=[O:2].C(=O)(O)[O-].[K+].[CH2:17]([CH:19]1[O:21][CH2:20]1)Br>CN(C=O)C>[OH:21][CH2:20][CH:19]1[O:11][C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=[CH:9][C:7]=2[O:8][CH2:17]1

参加物

5

反応物 3

HCID 18430EpibromohydrinHCID 516893Potassium BicarbonateHCID 35051094-Nitrocatechol

生成物 1

HCID 12736685(7-Nitro-2,3-dihydro-1,4-benzodioxin-2-yl)methanol収率 3.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
90 °C

実験手順

17.6 g 4-nitrocatechol and 11.0 g potassium bicarbonate were stirred in 200 ml DMF at 10° C. 13.99 g epibromohydrin in 10 ml DMF were added dropwise and stirring was continued at 60° C. for another 17 hrs. DMF was evaporated and the residue diluted with 50 ml water and extracted with ethyl acetate. The combined organic phases were washed with caustic soda and water., dried and evaporated. The crude oily product was heated to 90° C. with 200 ml toluene and the supernatant decanted from insoluble parts. After cooling to RT the solution is again decanted from insoluble oils and left at RT for 3 d. A first crop of 0.75 g crystalline title product was obtained. The mother liquor was evaporated and the residue dissolved in 20 dichloromethane at RT. Seeding and chilling to 0° C. yielded another 2.78 g crystalline title product.

後処理

  1. customDMF was evaporated
  2. additionthe residue diluted with 50 ml water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic phases were washed with caustic soda and water
  5. custom, dried
  6. customevaporated
  7. customthe supernatant decanted from insoluble parts
  8. temperatureAfter cooling to RT the solution
  9. customis again decanted from insoluble oils
  10. waitleft at RT for 3 d

出典と根拠

ORDレコード
ord-bc98e3ec676947a9ac1de87fe6360973
出典データセット
uspto-grants-2006_08
特許番号
US07091345B2

関連ノート

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