Ethanol → 4-(Benzyloxy)benzoic acid

HRID 1833926Notes

Reaction equation

HRID 1833926 reaction equation
N[C:2]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)=[O:3].C([OH:20])C>[OH-].[Na+]>[C:2]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([OH:20])=[O:3]

Participants

4

Reactant 2

HCID 702EthanolHCID 27264314-Benzyloxybenzamide

Product 1

HCID 738804-(Benzyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 4-aminocarbonylphenoxy phenyl methane (10g) in ethanol (100ml) and sodium hydroxide (100ml., 10N) was heated under reflux with vigorous stirring for 24hrs. The reaction mixture was cooled, the precipitated sodium salt was filtered off washed with a little water then converted to 4-carboxyphenoxy phenyl methane by boiling under reflux with concentrated hydrochloric acid (100ml) for 6hr. Dilution of the cooled mixture and extraction with ether yielded 4-carboxyphenoxy phenyl methane, m.p. 188°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureThe reaction mixture was cooled
  4. filtrationthe precipitated sodium salt was filtered off
  5. washwashed with a little water
  6. temperatureunder reflux with concentrated hydrochloric acid (100ml) for 6hr
  7. extractionDilution of the cooled mixture and extraction with ether

Sources & evidence

ORD record
ord-586d8f06b3894ed3a61fc7da1e804065
Source dataset
uspto-grants-1978_01
Patent number
US04067892

Reaction notes

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