Sulfuric Acid → 2-(Benzyloxymethyl)-6-chromanecarboxylic acid

HRID 1603873노트

반응식

HRID 1603873 반응식
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:20]=[O:21])[CH:16]=2)[O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=[O:24].OS(O)(=O)=O.O=[Cr](=O)=O.S(=O)(=O)(O)O>CC(C)=O.[O-2].[O-2].[O-2].[Cr+6].O.C(O)(C)C>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:20]([OH:24])=[O:21])[CH:16]=2)[O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 3

HCID 1118Sulfuric AcidHCID 196063282-(Benzyloxymethyl)-6-chromanecarbaldehydeHCID 131709961Jones' reagent

생성물 1

HCID 196062512-(Benzyloxymethyl)-6-chromanecarboxylic acid수율 60%

시약·촉매·용매 4

HCID 10219390chromium (VI) trioxide촉매HCID 180Acetone용매HCID 962Water용매2회HCID 3776Isopropanol용매

실험 절차

A solution of 2-(benzyloxymethyl)-6-chromane-carbaldehyde (0.921 g, 3.27 mmol) in acetone (5 ml) was added at 0° C. with Jones reagent, consisting of a mixture of chromium trioxide (0.326 g, 3.27 mmol), water (0.95 ml) and concentrated sulfuric acid (0.27 ml). The mixture was left under stirring at room temperature for 18 h. After that, a mixture of isopropyl alcohol (10 ml) and water (50 ml) was added, extracting with ethyl ether (3×30 ml). The organic phase was dried and the solvents were evaporated off under reduced pressure to obtain a residue which was purified by chromatography through a silica gel column. Eluting with hexane:ethyl acetate, 7:3, 0.580 g of the title compound were obtained (60% yield).

후처리

  1. waitThe mixture was left
  2. additionwas added
  3. extractionextracting with ethyl ether (3×30 ml)
  4. customThe organic phase was dried
  5. customthe solvents were evaporated off under reduced pressure
  6. customto obtain a residue which
  7. customwas purified by chromatography through a silica gel column
  8. washEluting with hexane

출처 및 근거

ORD 기록
ord-de6a7e728a8449c2aa7cab913f494e7c
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05990142

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