Water → 2-(4-Chlorophenoxy)-1,3-propanediol

HRID 1613363노트

반응식

HRID 1613363 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH:11]([O:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)[C:12](OCC)=[O:13])C.O.[OH-].[Na+]>O1CCCC1>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([O:17][CH:11]([CH2:12][OH:13])[CH2:10][OH:9])=[CH:23][CH:22]=1

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 18402089Diethyl 2-(4-chlorophenoxy)malonateHCID 21226445Aluminium lithium hydride2회

생성물 1

HCID 191086872-(4-Chlorophenoxy)-1,3-propanediol수율 45%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred slurry of 11.4 g (0.3 mole) of lithium aluminum hydride (LAH) in 200 ml of freshly distilled (from LAH) tetrahydrofuran (THF) was added dropwise a solution of 57.3 g (0.2 mole) of 2-(4-chlorophenoxy)-1,3-propanedioic acid diethyl ester (CA 59:5051f (1963); Mamaev and Mikhaleva, Isv. Sibirsk. Otd. Akad. Nauk. SSSR, 145-8 (1962)) in 150 ml of THF at such a rate that a gentle reflux was maintained. The mixture was stirred at ambient temperature for 5 hr and then the excess LAH was decomposed with successive, cautious, dropwise additions of 11.4 ml of water, 11.4 ml of a 15% sodium hydroxide solution, and 34 ml of water. A gelatinous precipitate developed which was filtered through Celite® with great difficulty. The filtrate was concentrated and the residue was purified by column chromatography on 500 g of silica gel eluted with 0-35% acetone in benzene. The appropriate fractions were combined and concentrated to give an oil which gradually crystallized. The solid was triturated with petroleum ether (30°-60° C.), collected by filtration, and dried to yield 18.2 g (45%) of white solid, mp 62°-64° C. (isopropyl ether).

후처리

  1. temperaturea gentle reflux
  2. temperaturewas maintained
  3. filtrationwas filtered through Celite® with great difficulty
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by column chromatography on 500 g of silica gel
  6. washeluted with 0-35% acetone in benzene
  7. concentrationconcentrated
  8. customto give an oil which
  9. customgradually crystallized
  10. customThe solid was triturated with petroleum ether (30°-60° C.)
  11. filtrationcollected by filtration
  12. customdried

출처 및 근거

ORD 기록
ord-0d56405811fe4c5fb7a6ab01515ff484
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05192785

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