Phloroglucinol → 5,7-Dihydroxy-2,2-dimethylchroman-4-one
Reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH:15][C:16]1[CH:21]=[C:20]([OH:22])[CH:19]=[C:18]([OH:23])[CH:17]=1.[CH3:24][C:25]([CH3:30])=[CH:26][C:27](O)=[O:28]>CS(O)(=O)=O>[OH:15][C:16]1[CH:21]=[C:20]([OH:22])[CH:19]=[C:18]2[C:17]=1[C:27](=[O:28])[CH2:26][C:25]([CH3:30])([CH3:24])[O:23]2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
40 ml of methanesulfonic acid was added to 1.99 g of diphosphorus pentoxide under nitrogen atmosphere. Thereafter, a mixture consisting of 3.15 g of 1,3,5-trihydroxybenzene and 3,3-dimethylacrylic acid was added to the reaction solution at 70° C. The reaction solution was stirred at 70° C. for 30 minutes and then cooled to a room temperature. The reaction solution was added to ice water, followed by extraction with ethyl acetate. The extract was washed with water and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain 2.81 g of the subject compound.
Workup
- additionwas added to the reaction solution at 70° C
- temperaturecooled to a room temperature
- extractionfollowed by extraction with ethyl acetate
- washThe extract was washed with water
- dry with materialThe organic layer was dried over magnesium sulfate
- concentrationconcentrated under a reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-e99c47404f834f2395e7687446602c1d
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07538123B2
Reaction notes
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