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

HRID 263925

반응식

HRID 263925 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-687f0b0c1912405d906505bd62dc3adb
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646149

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