Water → Octanoic Acid

HRID 465542Notes

Reaction equation

HRID 465542 reaction equation
ClC1C=CC(S(N[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](CCCCCC2C=NC=CC=2)(C(OCC)=O)[C:19]([O:21]CC)=[O:20])(=O)=O)=CC=1.O.C(=O)(O)[O-].[Na+]>Cl.C(O)(=O)C>[C:19]([OH:21])(=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]

Participants

6

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 14986647HCID 14986647, compound

Product 1

HCID 379Octanoic Acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1.4 g of ethyl 8-(p-chlorophenylsulfonamido)-2-[5-(3-pyridyl)-pentyl]-2-(ethoxycarbonyl)-octanoate in 50 ml of 6N HCl and 10 ml of acetic acid is heated to reflux for 23 h after which time it is evaporated to give an oil. This is treated with water, the solution is neutralized with solid sodium bicarbonate to a pH of 6.4 and extracted with ethyl acetate. The ethyl acetate extract is dried over magnesium sulfate, filtered and concentrated to give crude product which is further purified by chromatography on silica gel [(1) ethyl acetate as eluent, (2) preparative thin layer chromatography with ethyl acetate/acetic acid 99.5:0.5] to give 8-(p-chlorophenylsulfonamido)-2-[5-(3-pyridyl)pentyl])-octanoic acid as an oil, NMR (CDCl3): delta 7.77 (d,2H), 7.4 (d,2H), 2.85 (t,2H), 2.55 (t,2H).

Workup

  1. temperatureto reflux for 23 h after which time it
  2. customis evaporated
  3. customto give an oil
  4. extractionextracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. dry with materialis dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give crude product which
  10. customis further purified by chromatography on silica gel [(1) ethyl acetate as eluent, (2) preparative thin layer chromatography with ethyl acetate/acetic acid 99.5:0.5]

Sources & evidence

ORD record
ord-1215031b17ca49ba890a5e64872f9c09
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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