Water → Benzaldehyde, 4-(phenylmethoxy)-

HRID 1504584Notes

Reaction equation

HRID 1504584 reaction equation
[C:1](#N)[CH3:2].[CH2:4](Br)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:12](=[O:15])([O-])[O-].[K+].[K+].C(Cl)Cl.[OH2:21]>>[CH2:4]([O:21][C:2]1[CH:1]=[CH:7][C:6]([CH:12]=[O:15])=[CH:5][CH:4]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 6344DichloromethaneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-Yield 88.7%

Procedure

In an acetonitrile (30 mL) solvent, benzyl bromide (1.95 mL, 16.40 mmol) was added to a solution including 4-hydroxybenzaldhehyde (2.0 g, 16.38 mmol) and potassium carbonate (3.40 g, 24.60 mmol), and the reaction mixture was refluxed for 1.5 hours. After cooling, the reaction mixture was distributed between methylene chloride and water. An organic layer was dried by using MgSO4 and filtered. The filtrate was evaporated, and the resultant solid was added to water. The solid was filtered and washed with water to obtain Compound 123b (3.082 g, 88.7%).

Workup

  1. temperaturethe reaction mixture was refluxed for 1.5 hours
  2. temperatureAfter cooling
  3. customAn organic layer was dried
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. additionthe resultant solid was added to water
  7. filtrationThe solid was filtered
  8. washwashed with water

Sources & evidence

ORD record
ord-7228e4a694ad44fab582b462040a5f4a
Source dataset
uspto-grants-2015_12
Patent number
US09216148B2

Reaction notes

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