Hydrochloric Acid → HCID 18620158, compound

HRID 1862625Notes

Reaction equation

HRID 1862625 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]([CH:19]=[CH2:20])=[CH:15][C:10]=1[C:11]([O:13]C)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]([CH:19]=[CH2:20])=[CH:15][C:10]=1[C:11]([OH:13])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18620104HCID 18620104, compound

Product 1

HCID 18620158HCID 18620158, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 2-benzyloxy-5-vinylbenzoate (1.95 g) in methanol (10 ml) was added 2N aqueous sodium hydroxide solution (7.6 ml) at room temperature, and the mixture was heated under reflux for 1 hour with stirring. The reaction mixture was acidified with 2N hydrochloric acid, and the resulting mixture was extracted with dichloromethane. The extract was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. Crystallization of the residue from a mixed solution of hexane and diethyl ether (2/1) gave 2-benzyloxy-5-vinylbenzoic acid (1.49 g)

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. extractionthe resulting mixture was extracted with dichloromethane
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customCrystallization of the residue from a mixed solution of hexane and diethyl ether (2/1)

Sources & evidence

ORD record
ord-dd083e212ff64d77918faacb536cef74
Source dataset
uspto-grants-2003_03
Patent number
US06538152B1

Reaction notes

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