Sulfuric Acid → HCID 54420690, compound

HRID 1870842Notes

Reaction equation

HRID 1870842 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)=[O:5].[CH:19](OCC)(OCC)[O:20]CC.S(=O)(=O)(O)O.[C:34](=O)(O)[O-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:18])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)([O:20][CH3:19])[O:5][CH3:34]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 31214Ethyl orthoformateHCID 516892Sodium BicarbonateHCID 18793943HCID 18793943, compound

Product 1

HCID 54420690HCID 54420690, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of biphenyl-4-yl-oxo-acetic acid methyl ester (A. T. Jeffries, et al., J. Org. Chem., 46, 2885(1981)) (10 g), triethyl orthoformate (43 ml), methanol (60 ml) and conc. sulfuric acid (3 ml) was heated under reflux for 8.5 hours under a nitrogen atmosphere. The resulting mixture was poured into a saturated aqueous sodium bicarbonate solution and the resulting mixture was subjected to extraction with diethyl ether. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried over sodium sulfate and thereafter concentrated under reduced pressure, to obtain the desired compound (10.5 g).

Workup

  1. temperatureunder reflux for 8.5 hours under a nitrogen atmosphere
  2. extractionthe resulting mixture was subjected to extraction with diethyl ether
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0cb32a167a074c0f80aa87d78b4838c2
Source dataset
uspto-grants-2000_08
Patent number
US06100260

Reaction notes

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