Acetic Anhydride → 6-Acetoxy-2-methoxy-2,5,7,8-tetramethylchroman

HRID 263925ノート

反応式

HRID 263925 の反応式
[C:1](OC(=O)C)(=[O:3])[CH3:2].[OH:8][C:9]1[C:10]([CH3:24])=[C:11]2[C:16](=[C:17]([CH3:20])[C:18]=1[CH3:19])[O:15][C:14]([O:22][CH3:23])([CH3:21])[CH2:13][CH2:12]2>N1C=CC=CC=1>[C:1]([O:8][C:9]1[C:10]([CH3:24])=[C:11]2[C:16](=[C:17]([CH3:20])[C:18]=1[CH3:19])[O:15][C:14]([O:22][CH3:23])([CH3:21])[CH2:13][CH2:12]2)(=[O:3])[CH3:2]

参加物

4

反応物 2

HCID 7918Acetic AnhydrideHCID 1037632H-1-Benzopyran-6-ol, 3,4-dihydro-2-methoxy-2,5,7,8-tetramethyl-

生成物 1

HCID 144156636-Acetoxy-2-methoxy-2,5,7,8-tetramethylchroman

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Acetic anhydride (135 mL) was added dropwise to a solution of 6-hydroxy-2-methoxy-2,5,7,8-tetramethylchroman (71.8 g, 303.85 mmol) in pyridine (90 mL) which was cooled by an ice/water bath. After the addition was complete, the reaction mixture was allowed to warm to ambient temperature. After stirring at ambient temperature for 18 h, the reaction mixture was added to 1 L of ice water. This mixture was allowed to stir for 2 h and was then extracted with diethyl ether (3×200 mL). The combined organics were washed with 2N HCl (200 mL), brine (200 mL), saturated sodium bicarbonate (200 mL) and brine (200 mL). The organic solution was dried (sodium sulfate) and concentrated in vacuo to give 74.11 g (87% crude yield) of a yellow solid which was used crude in the next reaction.

後処理

  1. temperaturewas cooled by an ice/water bath
  2. additionAfter the addition
  3. stirringto stir for 2 h
  4. extractionwas then extracted with diethyl ether (3×200 mL)
  5. washThe combined organics were washed with 2N HCl (200 mL), brine (200 mL), saturated sodium bicarbonate (200 mL) and brine (200 mL)
  6. dry with materialThe organic solution was dried (sodium sulfate)
  7. concentrationconcentrated in vacuo
  8. customto give 74.11 g (87% crude yield) of a yellow solid which
  9. customin the next reaction

出典と根拠

ORDレコード
ord-687f0b0c1912405d906505bd62dc3adb
出典データセット
uspto-grants-1997_07
特許番号
US05646149

反応ノート

読み込み中…