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

HRID 268407ノート

反応式

HRID 268407 の反応式
[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].C([O-])(O)=O.[Na+]>O1CCCC1.O>[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]

参加物

7

反応物 4

HCID 1049PyridineHCID 55926-Hydroxy-2,5,7,8-tetramethylchroman-2-acetic acidHCID 7918Acetic AnhydrideHCID 516892Sodium Bicarbonate

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

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 N2 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 H2O and 100 ml. of tetrahydrofuran was added 166 g. (2.0 mol.) of NaHCO3. 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 an 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.

後処理

  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

出典と根拠

ORDレコード
ord-f7f0f9db3dc94978bb17d53c47a16c90
出典データセット
uspto-grants-1976_03
特許番号
US03947473

反応ノート

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