Hydrochloric Acid → HCID 22988695, compound

HRID 987320Notes

Reaction equation

HRID 987320 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:32])[CH:6]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([S:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:21][CH:20]=2)=[CH:12][CH:11]=1)[CH2:7][CH3:8].[OH-].[Li+].Cl>O1CCOCC1.O>[C:26]1([S:25][C:22]2[CH:23]=[CH:24][C:19]([CH2:18][CH2:17][O:16][C:13]3[CH:12]=[CH:11][C:10]([CH2:9][CH:6]([CH2:7][CH3:8])[C:5]([OH:32])=[O:4])=[CH:15][CH:14]=3)=[CH:20][CH:21]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 14798Sodium HydroxideHCID 54410975HCID 54410975, compound

Product 1

HCID 22988695HCID 22988695, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Sodium hydroxide (3 ml, 1M) was slowly added to a solution of 2-{4-[2-(4-phenylsulfanylphenyl)ethoxy]benzyl}butanoic acid methyl ester (described in Example 79) (0.59 g, 1.4 mmole) in dioxan (12 ml). The reaction mixture was stirred at room temperature for 12 hours, then at 50° C. for 4 hours. Lithium hydroxide (50 mg) was added and the mixture was stirred at 70° C. for 24 hours. The reaction mixture was acidified with hydrochloric acid (6 M), water (20 ml) was added and the product was extracted with ethyl acetate (2×25 ml), washed with water (25 ml), dried (sodium sulfate) and the solvent was evaporated in vacuo to give 0.53 g (yield 93%) of the desired product.

Workup

  1. waitat 50° C. for 4 hours
  2. stirringthe mixture was stirred at 70° C. for 24 hours
  3. additionwas added
  4. extractionthe product was extracted with ethyl acetate (2×25 ml)
  5. washwashed with water (25 ml)
  6. dry with materialdried (sodium sulfate)
  7. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-097af97c2c134ab281c6be494cd56dab
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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