Potassium Carbonate → HCID 14528680, compound

HRID 223720Notes

Reaction equation

HRID 223720 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:13](=[O:16])([O-])[O-:14].[K+].[K+]>CN(C)C=O>[C:13]([CH:3]1[CH2:2][CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][S:1][C:2]1[CH:3]=[C:4]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1)([OH:14])=[O:16]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 14528677HCID 14528677, compound

Product 1

HCID 14528680HCID 14528680, compoundYield 192.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
170 °C

Procedure

To 2-(3-mercaptophenyl)propionic acid (2.7 g) were added cis-2-(hydroxymethyl)cyclohexanecarboxylic acid lactone (2.5 g), potassium carbonate (2.5 g) and dimethylformamide (25 ml). The mixture was heated with stirring for 3 hours in an oil bath maintained at 170° C. and evaporated to dryness under reduced pressure. The residue was dissolved in water, acidified with hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layers were washed with water, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure to give the title compound (4.6 g) as an oil. IR νmaxfilm cm-1 : 1700 (C=O). MS m/e: 322 (M+).

Workup

  1. temperatureThe mixture was heated
  2. customevaporated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layers were washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-6347d1f82a064e9f8d32ac54dafecf38
Source dataset
uspto-grants-1982_10
Patent number
US04356186

Reaction notes

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