m-Chloroperbenzoic acid → 2,3-Dihydro-1,4-benzodioxin-6-ol

HRID 38381

反応式

HRID 38381 の反応式
[O:1]1[C:6]2[CH:7]=[CH:8][C:9](C=O)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:21])C=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([OH:21])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 70297m-Chloroperbenzoic acidHCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 516892Sodium Bicarbonate

生成物 1

HCID 91152732,3-Dihydro-1,4-benzodioxin-6-ol収率 96.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

To a solution of 2,3-dihydro-benzo[1,4]dioxin-6-carboxaldehyde (30.0 g, 183 mmol) in 500 ml CH2Cl2 was added mCPBA (37.85 g, 219 mmol). The suspension was heated to 50° C. After 16 h saturated NaHCO3 was added and the mixture was extracted with CH2Cl2 The combined organics were concentrated in vacuo and taken up in MeOH and 200 ml 4M NaOH was added. After 2 h the mixture was acidified with 4M HCl and extracted with ethyl acetate. The combined organics were washed with saturated NaHCO3, washed with brine, concentrated in vacuo, and taken up in CH2Cl2. The solution was filtered to remove the precipitate. The resulting solution was stirred with saturated NaHCO3 for 1 h, separated, dried over MgSO4, filtered and concentrated in vacuo to give 2,3-dihydro-benzo[1,4]dioxin-6-ol (26.92 g, 94%).

後処理

  1. extractionthe mixture was extracted with CH2Cl2 The combined
  2. concentrationorganics were concentrated in vacuo
  3. addition200 ml 4M NaOH was added
  4. extractionextracted with ethyl acetate
  5. washThe combined organics were washed with saturated NaHCO3
  6. washwashed with brine
  7. concentrationconcentrated in vacuo
  8. filtrationThe solution was filtered
  9. customto remove the precipitate
  10. customseparated
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-14d17fc460f14beea1aad9fb14bea198
出典データセット
uspto-grants-2013_09
特許番号
US08524725B2

関連ノート

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