Sulfuric Acid → HCID 68709437, compound

HRID 2376259Notes

Reaction equation

O[CH:2]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH3:14])[CH3:13])=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[CH3:15][C:16]1[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=1O.S(=O)(=O)(O)O>O>[CH:12]([C:9]1[CH:10]=[CH:11][C:6]([CH:2]2[C:18]3[C:19]([CH3:23])=[CH:20][C:21]([CH3:22])=[C:16]([CH3:15])[C:17]=3[O:5][C:3]2=[O:4])=[CH:7][CH:8]=1)([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 115 °C

Procedure

To a mixture of hydroxy(4-isopropylphenyl)acetic acid synthesized in Reference Example 1 (11.8 g, 60.8 mmol) and 2,3,5-trimethylphenol (12.4 g, 91.2 mmol) was added 70% sulfuric acid (10 mL) at room temperature, and the mixture was stirred at 115° C. for 12 hours. The mixture was added to water and was extracted with diisopropyl ether. The extract was washed with water and a saturated sodium hydrogen carbonate solution, and then was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain a residue, which was purified by silica gel column chromatography (hexane ethyl acetate=8:1) to obtain 10.9 g (yield 65%) of the title compound. Melting point: 107-108° C. (hexane-ethyl acetate).

Workup

extractionwas extracted with diisopropyl ether
washThe extract was washed with water
dry with materiala saturated sodium hydrogen carbonate solution, and then was dried over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure
customto obtain a residue, which
customwas purified by silica gel column chromatography (hexane ethyl acetate=8:1)

Sources & evidence

ORD record: ord-6fd1ef90f4664c529dc7ec8769d0b529
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465815B2

Reaction notes

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