Hydrochloric Acid → 5-(9-oxo-9H-xanthen-2-yloxy)pentanoic acid

HRID 1464585Notes

Reaction equation

HRID 1464585 reaction equation
[O:1]=[C:2]1[C:15]2[CH:14]=[C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23]CC)=[O:22])[CH:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[OH-].[Na+].Cl>CCO>[O:1]=[C:2]1[C:15]2[CH:14]=[C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2818242Pentanoic acid, 5-[(9-oxo-9H-xanthen-2-yl)oxy]-, ethyl ester

Product 1

HCID 28182415-(9-oxo-9H-xanthen-2-yloxy)pentanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 5-(9-oxoxanthen-2-oxy)valerate (7.0 g, 21 mmol) prepared as described above was suspended in 95% EtOH (50 mL), and 4 N aqueous NaOH (50 mL, 0.2 mmol) was added. The reaction mixture was homogeneous within 1h, and saponification proceeded at 25° C. for a total of 4 h. Subsequently, 12 N aqueous HCl (17 mL) was added with cooling to adjust the pH to 3. A light-gray precipitate formed, which was collected, washed with water (3×10 mL), and dried in vacuo over P2O5, to give the free acid product. Yield: 6.1 g (94%). A small amount of the product was recrystallized from n-hexane-EtOH (10:1) for elemental analysis in accordance with structure. Light beige needles, m.p. 151-152° C.

Workup

  1. customproceeded at 25° C. for a total of 4 h
  2. temperaturewith cooling
  3. customA light-gray precipitate formed
  4. customwhich was collected
  5. washwashed with water (3×10 mL)
  6. dry with materialdried in vacuo over P2O5
  7. customto give the free acid product
  8. customA small amount of the product was recrystallized from n-hexane-EtOH (10:1) for elemental analysis in accordance with structure

Sources & evidence

ORD record
ord-9cb31cc186d34d02b1822f2e3c25f95e
Source dataset
uspto-grants-1994_04
Patent number
US05306562

Reaction notes

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