Methanol → 5-Propyloxy-pentan-2-ol
Reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][CH3:10])(=[O:3])[CH3:2].CO.[BH4-].[Na+]>[OH-].[Na+]>[CH2:8]([O:7][CH2:6][CH2:5][CH2:4][CH:1]([OH:3])[CH3:2])[CH2:9][CH3:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To 34.8 g of the 3-acetyl-1-propyloxy-propane obtained in (1) was added 50 ml of methanol, and a solution of 44.4 g of NaBH4 in 8% sodium hydroxide was dropwise added at room temperature. After the reaction, the methanol was distilled off, 200 ml of water was added, and the mixture was extracted with ether. An organic layer was washed with water and dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was filtered off, then, the ether was distilled off, and the remainder was distilled under vacuum for isolation and purification (104° C./20 mmHg; yield 40%).
Workup
- customAfter the reaction
- distillationthe methanol was distilled off
- addition200 ml of water was added
- extractionthe mixture was extracted with ether
- washAn organic layer was washed with water
- dry with materialdried over anhydrous sodium sulfate
- filtrationThe anhydrous sodium sulfate was filtered off
- distillationthe ether was distilled off
- distillationthe remainder was distilled under vacuum for isolation and purification (104° C./20 mmHg; yield 40%)
Sources & evidence
- ORD record
- ord-bbd7091f7cbd421cad7d91db12f36a29
- Source dataset
- uspto-grants-2000_08
- Patent number
- US06103517
Reaction notes
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