Ethyl Acetate → HCID 57368010, compound

HRID 1844060Notes

Reaction equation

HRID 1844060 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])[CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11].C(OCC)(=O)C>C(O)C.CCCCCC>[Cl:3][C:4]1[CH:5]=[C:6]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 66802079HCID 66802079, compound

Product 1

HCID 57368010HCID 57368010, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Procedure

1N NaOH solution was added to a stirred solution of ethyl 3-(3-chloro-4-(trifluoromethyl)phenyl)propanoate (I-85b: 4.8 g, 17.8 mmol) in ethanol and the resulting mixture was stirred at room temperature for 1 hour. The reaction was monitored by TLC (2% ethyl acetate in hexane). The reaction mixture was concentrated under reduced pressure, quenched with ice, acidified with 1N HCl and extracted with DCM (2×150 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford the product 4.2 g (97.6%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customquenched with ice
  3. extractionextracted with DCM (2×150 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-09160e74f66e407cbca5adc4402ce3a7
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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