Hydrochloric Acid → 3-(2,6-Dimethylbenzyloxy)benzoic acid

HRID 1820941Notes

Reaction equation

HRID 1820941 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:5]=1[CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=1)[C:11]([O:13]CC)=[O:12].Cl>>[CH3:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:4]([CH3:3])[C:5]=1[CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=1)[C:11]([OH:13])=[O:12]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10062422Ethyl 3-(2,6-dimethylbenzyloxy)benzoate

Product 1

HCID 117771683-(2,6-Dimethylbenzyloxy)benzoic acid

Procedure

1N NaOH (86 ml) was added to a stirred solution of Ethyl 3-(2,6-dimethylbenzyloxy)benzoate (Step A, 16.31 g, 57.4 mmol) in absolute alcohol (150 ml). After 3 hours of stirring at room temperature, the reaction mixture was acidified with 1M HCl and concentrated in vacuuo. The organic residue was taken into chloroform and washed with 1N HCl, dried over Na2SO4, filtered, concentrated and purified by flash chromatography using chloroform:methanol (95:5 spiked with acetic acid) as elutent.

Workup

  1. concentrationconcentrated in vacuuo
  2. washwashed with 1N HCl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-d2254e2e68224503a6254554f9d469ce
Source dataset
uspto-grants-2009_10
Patent number
US07605181B2

Reaction notes

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