Sulfuric Acid → HCID 68710706, compound

HRID 2376364Notes

Reaction equation

HRID 2376364 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].[Br:15][C:16]1[C:17]([CH3:25])=[C:18](O)[CH:19]=[C:20]([CH3:23])[C:21]=1[CH3:22].S(=O)(=O)(O)O>O>[Br:15][C:16]1[C:21]([CH3:22])=[C:20]([CH3:23])[C:19]2[CH:2]([C:6]3[CH:11]=[CH:10][C:9]([CH:12]([CH3:14])[CH3:13])=[CH:8][CH:7]=3)[C:3](=[O:4])[O:5][C:18]=2[C:17]=1[CH3:25]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 229355983-Bromo-2,4,5-trimethylphenolHCID 23423233Hydroxy(4-isopropylphenyl)acetic acid

Product 1

HCID 68710706HCID 68710706, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

To a mixture of hydroxy(4-isopropylphenyl)acetic acid (10.0 g, 46.5 mmol) synthesized in Reference Example 1 and 3-bromo-2,4,5-trimethylphenol synthesized in Reference Example 68 (8.2 g, 42.2 mmol) was added 70% sulfuric acid (10 mL) at room temperature, and the mixture was stirred at 115° C. for 4 hours. The mixture was added to water, which 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 the residue, which was purified by silica gel column chromatography (ethyl acetate:hexane=1:8) to obtain 6-bromo-3-(4-isopropylphenyl)-4,5,7-trimethyl-1-benzofuran-2 (3H)-one. To a solution of the compound in THF (80 mL) was added lithium aluminum hydride (2.40 g, 63.3 mmol) at 0° C., and the mixture was heated under reflux for 1 hour. Water was added to the reaction solution, and the product was extracted with ethyl acetate. The combined extract was washed with water, dried over magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was crystallized from hexane-ethyl acetate to obtain 15.5 g (yield 97%) of the title compound. Melting point: 96-97° C.

Workup

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

Sources & evidence

ORD record
ord-91e18fa9c190463eb68ab707e373ebea
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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