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

HRID 1603873ノート

反応式

HRID 1603873 の反応式
[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

参加物

8

反応物 3

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

生成物 1

HCID 196062512-(Benzyloxymethyl)-6-chromanecarboxylic acid収率 60%

試薬・触媒・溶媒 4

HCID 10219390chromium (VI) trioxide触媒HCID 180Acetone溶媒HCID 962Water溶媒2 回HCID 3776Isopropanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-de6a7e728a8449c2aa7cab913f494e7c
出典データセット
uspto-grants-1999_11
特許番号
US05990142

反応ノート

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