反応 #410120

反応方程式

methyl (RS)-5-(3-benzyloxyphenyl)-5-oxo-4-(2-methylphenyl)-pentanoate

→

methyl (RS)-5-(3-hydroxyphenyl)-5-oxo-4-(2-methylphenyl)pentanoate

収率 60.8%

溶媒

methanol

methyl acetate

hydrochloric acid

反応条件

後処理

1. 1
   ろ過The suspension is filtered
2. 2
   その他evaporated
3. 3
   workup.DISSOLUTIONThe residue is dissolved in ethyl acetate
4. 4
   洗浄washed with water
5. 5
   その他dried
6. 6
   その他evaporated
7. 7
   その他the residue is recrystallised from a mixture of ethyl acetate and cyclohexane

実験手順

A solution of methyl (RS)-5-(3-benzyloxyphenyl)-5-oxo-4-(2-methylphenyl)-pentanoate (46 g) in methanol (250 mL), methyl acetate (250 mL) and concentrated hydrochloric acid (25 mL) is treated with palladium on carbon catalyst (5%; 1.5 g) and shaken under hydrogen at atmospheric pressure and room temperature for 2 hours. The suspension is filtered, and evaporated. The residue is dissolved in ethyl acetate, washed with water, dried and evaporated, and the residue is recrystallised from a mixture of ethyl acetate and cyclohexane, giving methyl (RS)-5-(3-hydroxyphenyl)-5-oxo-4-(2-methylphenyl)pentanoate as colourless crystals (21.7 g), m.p. 101-103° C.

出典