Sodium Hydroxide → 5-(4-Formyl-3,5-dimethoxyphenoxy)valeric acid

HRID 1268628Notes

Reaction equation

HRID 1268628 reaction equation
[CH:1]([C:3]1[C:18]([O:19][CH3:20])=[CH:17][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14]CC)=[O:13])=[CH:5][C:4]=1[O:21][CH3:22])=[O:2].[OH-].[Na+]>CO>[CH:1]([C:3]1[C:4]([O:21][CH3:22])=[CH:5][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:17][C:18]=1[O:19][CH3:20])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11001390Pentanoic acid, 5-(4-formyl-3,5-dimethoxyphenoxy)-, ethyl ester

Product 1

HCID 138763995-(4-Formyl-3,5-dimethoxyphenoxy)valeric acidYield 77.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 5-(4-formyl-3,5-dimethoxyphenoxy)valerate (37 g, 119 mmol) in methanol (200 mL) was added 4 N sodium hydroxide (200 mL) and the mixture was stirred for 2 h. The methanol was removed in vacuo, water (100 mL) was added and the mixture was washed with ethyl acetate (100 mL) and dichloromethane (2×100 mL). The aqueous layer was acidified with 12 N hydrochloric acid until pH˜3 and extracted with ethyl acetate (2×200 mL). The combined organic layers were washed with brine (2×50 mL), dried (magnesium sulfate) and concentrated in vacuo. The obtained product was recrystallized from ethanol to give 26 g of 5-(4-formyl-3,5-dimethoxyphenoxy)valeric acid.

Workup

  1. customThe methanol was removed in vacuo, water (100 mL)
  2. additionwas added
  3. washthe mixture was washed with ethyl acetate (100 mL) and dichloromethane (2×100 mL)
  4. extractionextracted with ethyl acetate (2×200 mL)
  5. washThe combined organic layers were washed with brine (2×50 mL)
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated in vacuo
  8. customThe obtained product was recrystallized from ethanol

Sources & evidence

ORD record
ord-c254bc91756041148792d9d1e4419f4e
Source dataset
uspto-grants-2003_04
Patent number
US06555570B2

Reaction notes

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