Hydrochloric Acid → 5-Chloromethylfurfural

HRID 262396

반응식

HRID 262396 반응식
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@H:7]([C@@H:9]([CH2:11]O)[OH:10])O)O)O.C(OS(C1C=CC=CC=1)(=O)=O)CCCCCCCCCCC.[Na].C1(C)C=CC=CC=1.[ClH:43]>[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.O>[Cl:43][CH2:11][C:9]1[O:10][C:3]([CH:2]=[O:1])=[CH:5][CH:7]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric Acid2회HCID 1140TolueneHCID 3037556(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 57371080Sodium dodecylbenzene sulphonate

생성물 1

HCID 741915-Chloromethylfurfural

시약·촉매·용매 2

HCID 8154Hexadecyltrimethylammonium chloride촉매HCID 962Water용매

실험 절차

To the same three-necked flask as in Example 1 were added 5 g (0.028 mole) of a commercially available D-(+)-galactose and two kinds of surface active agent, i.e., 89.6 mg (0.00028 mole) of cetyltrimethylammonium chloride and 97.6 mg (0.00028 mole) of sodium laurylbenzenesulfonate. Then, 30 ml of toluene was added thereto and the mixture was stirred to make a suspension. Thereafter, about 6 ml of 35% aqueous hydrochloric acid was added dropwise from a dropping funnel over about 1 hour. A slight excess of hydrogen chloride was then slowly passed therethrough at 50° C. over 3 hours with stirring. After stirring was continued for a further 5 hours, the reaction solution was diluted with a little water and filtered through Celite while being washed with toluene. The toluene layer was neutralized, dried and concentrated to obtain about 1.9 g (theoretical yield 4.01 g) of 5-chloromethylfurfural as a crude product.

후처리

  1. stirringat 50° C. over 3 hours with stirring
  2. stirringAfter stirring
  3. filtrationfiltered through Celite
  4. washwhile being washed with toluene
  5. customdried
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-37b182d5d2eb41d79c8e5f2a89c4a45a
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04154744

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