Water → HCID 11344558, compound

HRID 1965912Notes

Reaction equation

HRID 1965912 reaction equation
C([O:3][CH:4](OCC)[CH2:5][O:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)C.C(O)(C(F)(F)F)=O.O>C(Cl)Cl>[O:3]=[CH:4][CH2:5][O:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 11230958HCID 11230958, compound

Product 1

HCID 11344558HCID 11344558, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-methoxybenzoic acid 2,2-diethoxy-ethyl ester (2b, 7.5 g, 28 mmol) in Cl2CH2 (75 ml) was treated with TFA (16.7 g, 11.3 ml, 140 mmol) and water (7.5 g, 7.5 ml, 28 mmol). The homogeneous solution was stirred for 3.5 hours at room temperature until GC showed complete reaction. The solution was concentrated in vacuo at 40° C. and then diluted with hexane and concentrated in vacuo several times to remove traces of TFA. The product, 4-methoxybenzoic acid 2-oxo-ethyl ester (2c, 5.9 g, 28 mmol, 100%) was isolated as an amorphous white solid and was used in the next step without any further purification. GC (Rt=11.0 min, 95%); 1H-NMR (CDCl3) δ: 9.72 (1H, s, HCO—), 8.06 (2H, d, J=8.8, ArH), 6.95 (2H, d, J=8.8, ArH), 4.87 (2H, s, HCOCH2O—), 3.87 (3H, s, OCH3).

Workup

  1. customreaction
  2. concentrationThe solution was concentrated in vacuo at 40° C.
  3. additiondiluted with hexane
  4. concentrationconcentrated in vacuo several times
  5. customto remove traces of TFA

Sources & evidence

ORD record
ord-834a073c154f4bc09bc950023a3d784a
Source dataset
uspto-grants-2013_04
Patent number
US08420354B2

Reaction notes

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