Hydrochloric Acid → 2-(4-Acetyl-2-n-propyl-3-hydroxyphenoxy)-2-(4-methoxyphenyl) acetic acid

HRID 1253337Notes

Reaction equation

HRID 1253337 reaction equation
[C:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][CH:9]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C:10]([O:12]CC)=[O:11])=[C:6]([CH2:25][CH2:26][CH3:27])[C:5]=1[OH:28])(=[O:3])[CH3:2].[OH-].[Na+].Cl>>[C:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][CH:9]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C:10]([OH:12])=[O:11])=[C:6]([CH2:25][CH2:26][CH3:27])[C:5]=1[OH:28])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15611123Ethyl 2-(4-acetyl-2-n-propyl-3-hydroxyphenoxy)-2-(4-methoxyphenyl)acetate

Product 1

HCID 156111242-(4-Acetyl-2-n-propyl-3-hydroxyphenoxy)-2-(4-methoxyphenyl) acetic acidYield 21.6%

Conditions

Temperature
80 °C

Procedure

A mixture of 4.5 g of Ethyl 2-(4-acetyl-2-n-propyl-3-hydroxyphenoxy)-2-(4-methoxyphenyl)acetate and 150 ml of 1 Normal sodium hydroxide was stirred at 80° C. for 2 hours. The reaction mixture was then cooled, acidified with 1 Normal hydrochloric acid, extracted with ethyl acetate, treated with charcoal, filtered and concentrated to dryness to give an oily residue which was crystallized from EtOAc/hexane, yielding 0.9 g of product, melting point 154°-156° C.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. extractionextracted with ethyl acetate
  3. additiontreated with charcoal
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customto give an oily residue which
  7. customwas crystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-90da32ac849947c0807063b633c9ad07
Source dataset
uspto-grants-1988_05
Patent number
US04748272

Reaction notes

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