Water → Ethyl 2-(4-hydroxyphenyl)propanoate

HRID 1626850Notes

Reaction equation

HRID 1626850 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+].O>C(Cl)Cl>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 57742134Ethyl 2-(4-(methoxymethoxy)phenyl)propanoate

Product 1

HCID 12785115Ethyl 2-(4-hydroxyphenyl)propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 2-(4-(methoxymethoxy)phenyl)propanoate (485 mg, 2.04 mmol) in methylene chloride (10 mL) was added trifluoroacetic acid (5 mL) at 0° C. The mixture was stirred for 40 minutes at 0° C. and then slowly added solid sodium bicarbonate (7.14 g) and water (100 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-39782d84758c4c64a6a80ae81bd1c772
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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