Hydrochloric Acid → HCID 15595183, compound

HRID 1906213Notes

Reaction equation

HRID 1906213 reaction equation
C[O:2][C:3](=[O:41])[CH2:4][O:5][C:6]1[CH:37]=[CH:36][C:9]2[C:10](=[O:35])[CH2:11][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[C:24]([OH:31])[C:23]=3[CH2:32][CH2:33][CH3:34])([CH3:14])[O:13][C:8]=2[C:7]=1[CH2:38][CH2:39][CH3:40].[OH-].[Na+].O.Cl>CO>[C:28]([C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:12]2([CH3:14])[CH2:11][C:10](=[O:35])[C:9]3[CH:36]=[CH:37][C:6]([O:5][CH2:4][C:3]([OH:41])=[O:2])=[C:7]([CH2:38][CH2:39][CH3:40])[C:8]=3[O:13]2)=[C:23]([CH2:32][CH2:33][CH3:34])[C:24]=1[OH:31])(=[O:30])[CH3:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14798Sodium HydroxideHCID 15595182HCID 15595182, compound

Product 1

HCID 15595183HCID 15595183, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.1 g of the ester product from Example 5 and 0.966 g of sodium hydroxide, in 36 ml of methanol and 9 ml of water was stirred at room temperature for 5.5 hours then poured into 60 ml of cold 1N hydrochloric acid and 150 ml of water. The mixture was extracted 3 times with ether. The combined ether extracts were washed with 3 portions of saturated aqueous sodium bicarbonate. Each bicarbonate wash was back-extracted with ether. The bicarbonate washes were combined and acidified to pH 1 with 3N hydrochloric acid. The acidic mixture was extracted 3 times with ethyl acetate. The ethyl acetate extracts were combined, washed with water and brine, dried (magnesium sulfate), filtered and concentrated in vacuo to yield 1.04 g of a yellow solid. This material was recrystallized from acetonitrile giving 0.82 g (76.6%) of rac.-[[2-[6-(4-acetyl-3-hydroxy-2-propylphenoxy)hexyl]-3,4-dihydro-2-methyl-4-oxo-8-propyl-2H-1-benzopyran-7-yl]oxy]acetic acid as a colorless solid, m.p. 120.5°-125.0° C.

Workup

  1. extractionThe mixture was extracted 3 times with ether
  2. washThe combined ether extracts were washed with 3 portions of saturated aqueous sodium bicarbonate
  3. washEach bicarbonate wash
  4. extractionwas back-extracted with ether
  5. extractionThe acidic mixture was extracted 3 times with ethyl acetate
  6. washwashed with water and brine
  7. dry with materialdried (magnesium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25874ac970c343d7925be8929879fad4
Source dataset
uspto-grants-1987_03
Patent number
US04650812

Reaction notes

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