gamma-Phenyl-gamma-butyrolactone → 8,9-Dimethoxy-7-hydroxy-6-methyl-5-phenyl-2-oxo-2,3,4,5-tetrahydrobenzoxepin

HRID 477759Notes

Reaction equation

HRID 477759 reaction equation
[CH3:1][O:2][C:3]1[C:9]([O:10][CH3:11])=[C:8]([OH:12])[C:7]([CH3:13])=[CH:6][C:4]=1[OH:5].[C:14]1([CH:20]2O[C:23](=[O:24])[CH2:22][CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH3:11][O:10][C:9]1[C:8]([OH:12])=[C:7]([CH3:13])[C:6]2[CH:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:21][CH2:22][C:23](=[O:24])[O:5][C:4]=2[C:3]=1[O:2][CH3:1]

Participants

3

Reactant 2

HCID 13884gamma-Phenyl-gamma-butyrolactoneHCID 111830272,3-Dimethoxy-5-methyl-1,4-benzenediol

Product 1

HCID 103818298,9-Dimethoxy-7-hydroxy-6-methyl-5-phenyl-2-oxo-2,3,4,5-tetrahydrobenzoxepinYield 18.6%

Procedure

An amount of 18.4 g of 2,3-dimethoxy-5-methylhydroquinone and 16.2 g of γ-phenyl-γ-butyrolactone was stirred in 150 ml of polyphosphoric acid at room temperature for 5 hours. The reaction mixture obtained was poured into ice-water and extracted with ether, and the ether extract was washed with water and then dried over magnesium sulfate and concentrated. The concentrated residue was purified by silica gel column chromatography/hexaneethyl acetate (2:1), and thus 6.10 g (18.6%) of the desired compound was obtained.

Workup

  1. customThe reaction mixture obtained
  2. extractionextracted with ether
  3. extractionthe ether extract
  4. washwas washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe concentrated residue was purified by silica gel column chromatography/hexaneethyl acetate (2:1)

Sources & evidence

ORD record
ord-89c3802d587a477fa78f911d88b113e9
Source dataset
uspto-grants-1989_12
Patent number
US04889853

Reaction notes

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