Dichloromethane → Benzyl glycidyl ether

HRID 1632290Notes

Reaction equation

HRID 1632290 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]=1

Participants

5

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

  1. customA 2,000 mL, 3-necked flask equipped with a mechanical stirrer
  2. customwas kept under 30° C
  3. additionAfter addition
  4. stirringthe reaction mixture was stirred 4 hours at 25° C
  5. dissolutionto dissolve the salts
  6. customThe organic phase was separated from the aqueous phase
  7. washwashed with ice water (3×500 mL)
  8. customdried

Sources & evidence

ORD record
ord-b64245fcfb8b46cab11d072a345906ab
Source dataset
uspto-grants-1984_10
Patent number
US04474963

Reaction notes

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