Hydrochloric Acid → HCID 15521369, compound

HRID 1457339Notes

Reaction equation

HRID 1457339 reaction equation
C([O:3][C:4](=[O:25])[CH:5]([CH2:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.Cl>>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([S:14]([CH2:13][CH:5]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([OH:25])=[O:3])(=[O:16])=[O:15])=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 15521368HCID 15521368, compound

Product 1

HCID 15521369HCID 15521369, compoundYield 89.7%

Conditions

Temperature
115 °C

Procedure

A mixture of 0.56 g (1.5 mmol) of 2-[(4-methoxybenzenesulfonyl)methyl]-3-phenyl-propanoic acid ethyl ester and 8 ml of 6N HCl is heated at 115° C. for 17 hours. The mixture is transferred to 100 ml of ice-water and extracted with two portions of ethyl acetate. The organic phase is extracted with three 50 mL portions of aqueous 5% sodium bicarbonate. The bicarbonate solution is poured over ice and acidified with concentrated HCl. The acidified aqueous mixture is extracted with three 50 mL portions of ethyl acetate and the combined organic extracts are concentrated in vacuo to yield 0.45 g of the title compound as a white solid.

Workup

  1. extractionextracted with two portions of ethyl acetate
  2. extractionThe organic phase is extracted with three 50 mL portions of aqueous 5% sodium bicarbonate
  3. additionThe bicarbonate solution is poured over ice
  4. extractionThe acidified aqueous mixture is extracted with three 50 mL portions of ethyl acetate
  5. concentrationthe combined organic extracts are concentrated in vacuo

Sources & evidence

ORD record
ord-b4d6b1647e0f4526bdcf4b043598474a
Source dataset
uspto-grants-1998_12
Patent number
US05847153

Reaction notes

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