Potassium Carbonate → 4-[4-(3-Hydroxypropyl)phenoxy]butanoic acid

HRID 1417772Notes

Reaction equation

HRID 1417772 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:19]=[CH:18][C:8]([O:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]CC)=[O:14])=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+]>>[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:19]=[CH:18][C:8]([O:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 11430Potassium CarbonateHCID 86752379HCID 86752379, compound

Product 1

HCID 542858664-[4-(3-Hydroxypropyl)phenoxy]butanoic acid

Procedure

After the method of Preparation 3, 4.13 g (15.51 mmol) of 4-[4-(3-hydroxypropyl)phenoxy]butanoic acid, ethyl ester is saponified with potassium carbonate to produce a solid. This is recrystallized from an ethyl acetate-hexane mixture giving 2.45 (66%) of 4-[4-(3-hydroxypropyl)phenoxy]butanoic acid as white crystals: m.p. 92°-94° C.; IR (KBr) 3420 (br.), 1710 cm-1 ; 1H-NMR (CDCl3) is consistent with the desired product; MS (CI) m/e 239 (M+ +H). Analysis calculated for C13H18O4 : C, 65.53; H, 7.61; O, 26.86. Found: C, 65.75; H, 7.87; O, 26.38.

Workup

  1. customto produce a solid
  2. customThis is recrystallized from an ethyl acetate-hexane mixture

Sources & evidence

ORD record
ord-77f590dd5e004037a1aee8de226bb4d1
Source dataset
uspto-grants-1999_03
Patent number
US05877296

Reaction notes

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