Sodium Hydroxide → HCID 19429801, compound

HRID 619552Notes

Reaction equation

HRID 619552 reaction equation
[C:1]([C:5]1[C:6]([OH:21])=[C:7]([CH2:15][CH2:16][C:17]([O:19]C)=[O:18])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([C:5]1[C:6]([OH:21])=[C:7]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH:8]=[C:9]([C:11]([CH3:12])([CH3:13])[CH3:14])[CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21807999HCID 21807999, compound

Product 1

HCID 19429801HCID 19429801, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Operating under a nitrogen current, 29.8 g of methyl 3-(3',5'-di-tert-butylhydroxyphenyl)propionate, 80 mL of ethanol, and 6 g of sodium hydroxide were introduced into a 0.5-L four-neck flask equipped with a stirrer, addition funnel, and thermometer and were stirred for 1 hour while heating under reflux. After the completion of the stirring period, the ethanol was removed by distillation and the reaction mass was then neutralized by the gradual addition of concentrated hydrochloric acid. 150 mL of a 1:1 liquid mixture of toluene and ethyl acetate was added followed by washing twice with water. The solvent was then distilled from the washed organic layer to give 27.2 g of 3-(3',5'-di-tert-butylhydroxyphenyl)propionic acid in crystalline form.

Workup

  1. customequipped with a stirrer, addition funnel
  2. temperaturewhile heating
  3. temperatureunder reflux
  4. customAfter the completion of the stirring period, the ethanol was removed by distillation
  5. additionthe reaction mass was then neutralized by the gradual addition of concentrated hydrochloric acid
  6. addition150 mL of a 1:1 liquid mixture of toluene and ethyl acetate
  7. additionwas added
  8. washby washing twice with water
  9. distillationThe solvent was then distilled from the washed organic layer

Sources & evidence

ORD record
ord-fa8008c69c454b2dba586c12b916e2f9
Source dataset
uspto-grants-1999_09
Patent number
US05959057

Reaction notes

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