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

HRID 1434667Notes

Reaction equation

HRID 1434667 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 vacuo. 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 vacuo
  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-82d98392b7fd430a8e589018948e8a60
Source dataset
uspto-grants-2009_11
Patent number
US07615575B2

Reaction notes

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