Water → HCID 22380608, compound

HRID 895648Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

2-(4-Carboxybenzyl)phenol (603 mg) was dissolved in isobutanol (3 ml), added with sulfuric acid (0.6 ml) and stirred at 80° C. for 3 hours. The reaction mixture was added with water (5 ml) and extracted twice with ethyl acetate (5 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=5:1) to obtain 318 mg of the title compound. Yield: 42%.

Workup

extractionextracted twice with ethyl acetate (5 ml)
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=5:1)

Sources & evidence

ORD record: ord-fb8cabb5ee4d4ffb9ae1bf10875cc5c2
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06916822B2

Reaction notes

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