Dichloromethane → Benzyl glycidyl ether
Reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([OH:13])[CH2:11]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl.[OH-].[Na+]>O>[CH2:1]([O:8][CH2:9][CH:10]1[O:13][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
A 2,000 mL, 3-necked flask equipped with a mechanical stirrer and thermometer was charged with 3-benzyloxy-2-hydroxypropyl chloride (353 g, 1.76 mol) and dichloromethane (1,000 mL). This mixture was stirred and cooled in an ice bath to ca. 5° C. Aqueous 50% NaOH (176 g) was added in portions while the temperature was kept under 30° C. After addition was complete, the reaction mixture was stirred 4 hours at 25° C. Water (1,000 mL) was added to dissolve the salts. The organic phase was separated from the aqueous phase, washed with ice water (3×500 mL), dried and reduced in vacuo to yield 263 g (92%) of pure 3-benzyloxy-1,2-epoxypropane.
Workup
- customA 2,000 mL, 3-necked flask equipped with a mechanical stirrer
- customwas kept under 30° C
- additionAfter addition
- stirringthe reaction mixture was stirred 4 hours at 25° C
- dissolutionto dissolve the salts
- customThe organic phase was separated from the aqueous phase
- washwashed with ice water (3×500 mL)
- customdried
Sources & evidence
- ORD record
- ord-b64245fcfb8b46cab11d072a345906ab
- Source dataset
- uspto-grants-1984_10
- Patent number
- US04474963
Reaction notes
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