Sulfuric Acid → HCID 68585617, compound

HRID 2240274Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:13]([CH:18]=[O:19])=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:8][CH:7]=1.CC(C)=[O:22].OS(O)(=O)=O.O=[Cr](=O)=O.S(=O)(=O)(O)O>CC(C)=O.O.[O-2].[O-2].[O-2].[Cr+6]>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:13]([C:18]([OH:22])=[O:19])=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The 4′-(2-methoxyethoxy)-1,1′-biphenyl-2-carbaldehyde from step b (3.691 g; 14.4 mmol) is dissolved in 45 ml of acetone, the mixture is cooled to 0° C. and 10.85 ml of Jones' reagent (solution of 3.5 g of chromium trioxide in a solution of 3.16 ml of sulfuric acid in 10 ml of water) are then added dropwise. After 1 hour at 0° C., the reaction medium is allowed to cool to room temperature over 8 hours. The reaction medium is evaporated to dryness, taken up in ether and filtered through silica. The organic phase is extracted with aqueous 1N sodium hydroxide solution, and the aqueous phase is then acidified with 1N hydrochloric acid and extracted with DCM. The organic phase is dried over sodium sulfate and evaporated to dryness to give 2.75 g of the expected product in the form of an oil.

Workup

temperatureto cool to room temperature over 8 hours
customThe reaction medium is evaporated to dryness
filtrationfiltered through silica
extractionThe organic phase is extracted with aqueous 1N sodium hydroxide solution
extractionextracted with DCM
dry with materialThe organic phase is dried over sodium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-1df1d743cef44d968e3d4944899b8aeb
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723358B2

Reaction notes

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