Hydrochloric Acid → Ethyl [4-(Benzyloxy)phenoxy]acetate

HRID 412610Notes

Reaction equation

HRID 412610 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].Cl>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7638MonobenzoneHCID 7748Ethyl bromoacetateHCID 24758Sodium hydride

Product 1

HCID 734886Ethyl [4-(Benzyloxy)phenoxy]acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-benzyloxyphenol (18.34 g) in tetrahydrofuran (150 ml) was added 60% sodium hydride (4.76 g) with ice-cooling, and the mixture was stirred at the same temperature for 15 min. Ethyl bromoacetate (14.2 ml) was added dropwise, and the mixture was stirred at room temperature for 16 hours. After completion of the reaction, 5% hydrochloric acid was added and the mixture was extracted with hexane. The extract was dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained solid was filtrated with hexane and dried under reduced pressure to give the title compound (21.78 g) as a white solid.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 16 hours
  3. additionwas added
  4. extractionthe mixture was extracted with hexane
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. filtrationthe obtained solid was filtrated with hexane
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-6925386723564c9091da70ccdc84ecd7
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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