Hydrochloric Acid → (1R,2R)-1-methoxy-2,3-dihydro-1H-inden-2-ol

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Reaction Conditions

Reaction Steps

Into a 500 ml four-neck flask, 120 ml of methanol was introduced and 16.4 g (0.304 mol) of sodium methoxide powder was dissolved therein. At 30° C., 20.0 g (0.152 mol) of cis-(±)-1,2-epoxyindan (VI) dissolved in 80 ml of methanol was dropwise added thereto in a period of 90 minutes. After this mixture was stirred at 30° C. for 5 hours, 100 ml of water was added thereto. The resulting mixture was neutralized with 270 ml of 1N hydrochloric acid and then methanol was distilled off under reduced pressure. The remaining mixture was extracted twice with 200 ml of dichloromethane. The extracted phase was dried for one night with sodium sulfuric anhydride. The dichloromethane phase was concentrated under pressure to yield 28.5 g of an orange oily substance. When it was purified by a silica gel column chromatography in which chloroform was used as a developing solvent, 16.32 g (yield: 65.5%) of trans-(±)-1-methoxyindan-2-ol (I') was obtained as a pale yellow oil. Its purity determined by an HPLC analysis was 95.4%.

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