Hydrochloric Acid → HCID 14421664, compound

HRID 2292220Notes

Reaction equation

HRID 2292220 reaction equation
[OH:1][C:2]1[C:3]([CH2:24][CH2:25][CH3:26])=[C:4]([CH:12]=[CH:13][C:14]=1[C:15](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[OH:22])[O:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#N.[OH-:27].[K+].Cl.C[OH:31].O>>[OH:1][C:2]1[C:3]([CH2:24][CH2:25][CH3:26])=[C:4]([CH:12]=[CH:13][C:14]=1[C:15](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[OH:22])[O:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:31])=[O:27]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 144216635-[3-Hydroxy-4-(2-hydroxybenzoyl)-2-propylphenoxy]pentanenitrileHCID 22242641Methanol--water (1/1)

Product 1

HCID 14421664HCID 14421664, compound

Procedure

A solution of 10 g of 5-[3-hydroxy-4-(2 -hydroxybenzoyl)-2-propylphenoxy]pentanenitrile and 12.9 g of potassium hydroxide in approximately 250 ml of 10% methanol/water was heated at reflux for 5 days. The solution was cooled to room temperature, acidified with hydrochloric acid. The crude product which precipitated was recovered by filtration and purified by high pressure liquid chromatography over silica gel eluting with a 30-40% ethyl acetate in hexane gradient containing 0.5% acetic acid. The appropriate fractions were combined, evaporated, and recrystallized from diethyl ether/hexane to provide 8.0 g of the desired title carboxylic acid, m.p. 88.5°-91.5° C.

Workup

  1. temperatureat reflux for 5 days
  2. customThe crude product which precipitated
  3. filtrationwas recovered by filtration
  4. custompurified by high pressure liquid chromatography over silica gel eluting with a 30-40% ethyl acetate in hexane gradient
  5. additioncontaining 0.5% acetic acid
  6. customevaporated
  7. customrecrystallized from diethyl ether/hexane

Sources & evidence

ORD record
ord-1660d86c0b6842ef832918ade210177a
Source dataset
uspto-grants-1989_01
Patent number
US04801616

Reaction notes

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