Pyridine → (+/-)-(6-Acetoxy-2,5,7,8-tetramethylchroman-2-yl)acetic acid

HRID 328843노트

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HRID 328843 반응식
[OH:1][C:2]1[C:3]([CH3:19])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][C:16]([OH:18])=[O:17])([CH3:14])[CH2:6][CH2:5]2.N1C=CC=CC=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>O1CCCC1>[C:26]([O:1][C:2]1[C:3]([CH3:19])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][C:16]([OH:18])=[O:17])([CH3:14])[CH2:6][CH2:5]2)(=[O:28])[CH3:27]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 55926-Hydroxy-2,5,7,8-tetramethylchroman-2-acetic acidHCID 7918Acetic Anhydride

생성물 1

HCID 21432320(+/-)-(6-Acetoxy-2,5,7,8-tetramethylchroman-2-yl)acetic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
25 °C

실험 절차

A mixture of 66.1 g. (0.25 mol.) of (±)-(6-hydroxy-2,5, 7,8-tetramethylchroman-2-yl) acetic acid and 250 ml. each of pyridine and acetic anhydride was stirred at 25° C. under N 2 for 20 hours and stripped of solvent at 40° C. to give an orangebrown oil. To a suspension of this material in 500 ml. of H 2 O and 100 ml. of tetrahydrofuran was added 166 g. (2.0 mol.) of NaHCO 3. the suspension was stirred at 25° C. for 4.0 hours, washed with ether, acidified with 2N-aqueous HCl and extracted with ether. The ether solutions were washed with saturated brine, dried over sodium sulfate and stripped of solvent to give (±)-(6-acetoxy-2,5,7,8-tetramethylchroman-2-yl) acetic acid as and orangeish resin. Crystallization from diethyl ether petroleum ether (b.p. 30°-60° C.) gave (±)-(6-acetoxy-2,5,7,8 -tetramethylchroman-2-yl) acetic acid as a granular white solid.

후처리

  1. additionA mixture of 66.1 g
  2. customstripped of solvent at 40° C.
  3. customto give an orangebrown oil
  4. additionTo a suspension of this material in 500 ml
  5. washwashed with ether
  6. extractionextracted with ether
  7. washThe ether solutions were washed with saturated brine
  8. dry with materialdried over sodium sulfate

출처 및 근거

ORD 기록
ord-e4a83194cf0a4ff59e253e7f72f2c558
출처 데이터셋
uspto-grants-1977_04
특허 번호
US04018799

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