تفاعل #559064

معادلة التفاعل

1-allyl-cyclohexane-1,3-dicarboxylic acid diethyl ester

1-Allyl-cyclohexane-1,3-dicarboxylic acid diethyl ester

potassium carbonate

quinuclidine

t-butanol

sodium sulfite

→

1-(2,3-dihydroxy-propyl)-cyclohexane-1,3-dicarboxylic acid diethyl ester

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   استخلاصAfter dilution with ethyl acetate, it was extracted
2. 2
   غسيلwashed with water and brine
3. 3
   تجفيفdried over Na2SO4
4. 4
   تركيزconcentrated under reduced pressure
5. 5
   أخرىThe resulting residue (224 g) was used in the next step without delay and without further purification

الإجراء التجريبي

To a solution of 1-allyl-cyclohexane-1,3-dicarboxylic acid diethyl ester from step 2 (250 g, 0.93 mol) in t-butanol (2.3 L) and water (2.3 L) was added potassium ferricyanide (920 g, 2.79 mol), potassium carbonate (386 g, 2.79 mol), potassium osmate dihydrate (4.75 g, 13 mmol) and quinuclidine (0.073 g, 7.0 mmol). The resulting dark colored solution was stirred at rt overnight and then quenched with portion-wise addition of sodium sulfite (1.05 kg, 8.37 mol). After dilution with ethyl acetate, it was extracted, washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure. The resulting residue (224 g) was used in the next step without delay and without further purification.

المصدر