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

HRID 1603873Notes

Reaction equation

HRID 1603873 reaction equation
[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

Participants

8

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-de6a7e728a8449c2aa7cab913f494e7c
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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