4-[4-(3-Hydroxypropyl)phenoxy]butanoic acid → HCID 54240155, compound

HRID 1417773Notes

Reaction equation

HRID 1417773 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:7][CH:6]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[O:1]=[CH:2][CH2:3][CH2:4][C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 542858664-[4-(3-Hydroxypropyl)phenoxy]butanoic acidHCID 178418287HCID 178418287, compound

Product 1

HCID 54240155HCID 54240155, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 1.19 g (5.00 mmol) sample of 4-[4-(3-hydroxypropyl)phenoxy]butanoic acid is dissolved with stirring in 250 mL of methylene dichloride. Next, 3.77 g (17.49 mmol) of pyridinium chlorochromate is added, the mixture is stirred for 4 hr, and then filtered through a celite pad. The reaction mixture is then diluted with an equal volume of ether, precipitating out salts. This mixture is then filtered through a silica gel pad, and the filtrate evaporated, giving a brown solid. The solid is recrystallized from an ether-hexane mixture producing 0.21 (18%) of 4-[4-(3-oxopropyl)phenoxy]butanoic acid as off-white crystals: m.p. 100°-03° C.; IR (KBr) 1715 cm-1 ; 1H-NMR (CDCl3) is consistent with the desired product; MS (CI) m/e 237 (M+ +H). Analysis calculated for C13H16O4 : C, 66.09; H, 6.83; O, 27.09. Found: C, 65.91; H, 6.72; O, 27.35.

Workup

  1. filtrationfiltered through a celite pad
  2. additionThe reaction mixture is then diluted with an equal volume of ether
  3. customprecipitating out salts
  4. filtrationThis mixture is then filtered through a silica gel pad
  5. customthe filtrate evaporated
  6. customgiving a brown solid
  7. customThe solid is recrystallized from an ether-hexane mixture

Sources & evidence

ORD record
ord-1fe3889780c24187bca23ac8af6ac56a
Source dataset
uspto-grants-1999_03
Patent number
US05877296

Reaction notes

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