Sodium Hydroxide → 2-Methoxy-6-methylbenzoic acid

HRID 2062227Notes

Reaction equation

HRID 2062227 reaction equation
C([O:3][C:4](=[O:14])[C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[O:12][CH3:13])C.[OH-].[Na+]>CCO>[CH3:13][O:12][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:5]=1[C:4]([OH:14])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 5910602-Methoxy-6-methyl-benzoic acid ethyl ester

Product 1

HCID 2731702-Methoxy-6-methylbenzoic acidYield 82.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Ethyl-2-methoxy-6-methylbenzoate (30.4 g, 0.157 mol) was added to 100 mL 3.2 M NaOH (2 equiv) and 150 mL hot EtOH. The mixture was refluxed overnight after which EtOH was removed in vacuo. The aqueous mixture was acidified with 5 M HCl to pH 3. CH2Cl2 (200 mL) was added, and the layers were separated. The water layer was extracted two times with 200 mL CH2Cl2, and the organic layers were combined and dried over Na2SO4. Filtering the Na2SO4 and concentrating the CH2Cl2 to dryness yielded 21.4 g (0.129 mol, 82.3%) of 2-methoxy-6-methyl-benzoic acid.

Workup

  1. customwas removed in vacuo
  2. additionCH2Cl2 (200 mL) was added
  3. customthe layers were separated
  4. extractionThe water layer was extracted two times with 200 mL CH2Cl2
  5. dry with materialdried over Na2SO4
  6. filtrationFiltering the Na2SO4
  7. concentrationconcentrating the CH2Cl2 to dryness

Sources & evidence

ORD record
ord-1cadacae7e734a3494b111671ec3f1eb
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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