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

HRID 2079924Notes

Reaction equation

HRID 2079924 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 0.1N 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 0.1N HCl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-0079d7755da241b9958de9c1e6d6c5fd
Source dataset
uspto-grants-2011_04
Patent number
US07932290B2

Reaction notes

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