Sodium Hydroxide → 4-(Cyclopropylmethoxy)-3-formylbenzoic acid

HRID 1776571Notes

Reaction equation

HRID 1776571 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][C:7]=2[CH:16]=[O:17])[CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([CH2:4][O:5][C:6]2[CH:15]=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=2[CH:16]=[O:17])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86679526Methyl 4-(cyclopropylmethoxy)-3-formylbenzoate

Product 1

HCID 866795274-(Cyclopropylmethoxy)-3-formylbenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

Methyl 4-(cyclopropylmethoxy)-3-formylbenzoate (2.6 g, 11.87 mmol) was dissolved in MeOH (40 mL), and NaOH 1 N (17 ml, 17.09 mmol) was added. The mixture was stirred at 40° C. for 4 hours. MeOH was evaporated under vacuum, and the reaction mixture was partitioned between EtOAc and HCl 1 M. The aqueous layer was extracted 3 times with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4, filtered and solvent removed under vacuum to give 2.42 g. (quantitative yield).

Workup

  1. customMeOH was evaporated under vacuum
  2. customthe reaction mixture was partitioned between EtOAc and HCl 1 M
  3. extractionThe aqueous layer was extracted 3 times with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customsolvent removed under vacuum
  8. customto give 2.42 g

Sources & evidence

ORD record
ord-902dd78605ec4c96b75118d9eadb2e3d
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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