Water → HCID 13356241, compound

HRID 1626868Notes

Reaction equation

HRID 1626868 reaction equation
COC[O:4][C:5]1[CH:6]=[C:7]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[CH:9][CH:10]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+].O>C(Cl)Cl>[OH:4][C:5]1[CH:6]=[C:7]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 57742132HCID 57742132, compound

Product 1

HCID 13356241HCID 13356241, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 2-(3-(methoxymethoxy)phenyl)propanoate (4.17 g, 17.5 mmol) in methylene chloride (80 mL) was added trifluoroacetic acid (40 mL) at 0° C. The mixture was stirred for 1 hr at 0° C. and then slowly added solid sodium bicarbonate (60 g) and water (250 mL) at 0° C. The mixture was extracted with methylene chloride. The organic layer was dried with MgSO4. The organic layer was filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography eluting with n-Hexane/EtOAc=4/1.

Workup

  1. customat 0° C
  2. extractionThe mixture was extracted with methylene chloride
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationThe organic layer was filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by column chromatography
  7. washeluting with n-Hexane/EtOAc=4/1

Sources & evidence

ORD record
ord-e519781b194f4dcd92b3dc43918d417b
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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