Hydrochloric Acid → HCID 21286976, compound

HRID 2231456Notes

Reaction equation

HRID 2231456 reaction equation
C([O:3][C:4](=[O:38])[CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[C:10]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[C:24]([OH:31])[C:23]=2[CH2:32][CH2:33][CH3:34])[C:9]=1[CH2:35][CH2:36][CH3:37])C.[Na].Cl>CO.[OH-].[Na+]>[C:14]([C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:6][CH2:5][C:4]([OH:38])=[O:3])=[C:9]([CH2:35][CH2:36][CH3:37])[C:10]=1[O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[C:24]([OH:31])[C:23]=1[CH2:32][CH2:33][CH3:34])(=[O:16])[CH3:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 57014320HCID 57014320, compound

Product 1

HCID 21286976HCID 21286976, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 5.4 g of racemic-[4-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]methylacetic acid ethyl ester in 100 ml of methanol and 50 ml of 1N sodium hydroxide was stirred at reflux for 2 hours. The methanol was removed in vacuo and the pH of the residue was adjusted to 2.0 with 6N hydrochloric acid. The gummy product was extracted with methylene chloride and the extract was dried over magnesium sulfate and concentrated in vacuo to an oil. The crude acid was dissolved in 50 ml of methanol and 10 ml of 1.0N sodium hydroxide was added. The methanol was removed in vacuo, 25 ml of water was added and the sodium salt (0.33 molar hydrate) of racemic-[4-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]methylacetic acid was filtered and dried to give 4.2 g (78%), mp 92°-95°. The sodium salt was converted with 1N hydrochloric acid to the acid, which crystallized on addition of hexane. Filtration gave racemic-[4-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]methylacetic acid, mp 123°-126°.

Workup

  1. temperatureat reflux for 2 hours
  2. customThe methanol was removed in vacuo
  3. extractionThe gummy product was extracted with methylene chloride
  4. dry with materialthe extract was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo to an oil
  6. dissolutionThe crude acid was dissolved in 50 ml of methanol
  7. addition10 ml of 1.0N sodium hydroxide was added
  8. customThe methanol was removed in vacuo, 25 ml of water
  9. additionwas added
  10. filtrationthe sodium salt (0.33 molar hydrate) of racemic-[4-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]methylacetic acid was filtered
  11. customdried
  12. customto give 4.2 g (78%), mp 92°-95°
  13. customcrystallized on addition of hexane
  14. filtrationFiltration

Sources & evidence

ORD record
ord-7375bbad3c584cafa83f9d6b43dfd407
Source dataset
uspto-grants-1988_11
Patent number
US04782176

Reaction notes

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