3-Phenylsalicylic acid → 2-(2,4-Dimethyl-3-pentyloxy)carbonyl-6-phenylphenol

HRID 610459Notes

Reaction equation

HRID 610459 reaction equation
CS([O:5][CH:6]([CH:10]([CH3:12])[CH3:11])[CH:7]([CH3:9])[CH3:8])(=O)=O.[C:13]1([C:19]2[CH:27]=[CH:26][CH:25]=[C:21]([C:22](O)=[O:23])[C:20]=2[OH:28])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH3:8][CH:7]([CH:6]([O:5][C:22]([C:21]1[CH:25]=[CH:26][CH:27]=[C:19]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:20]=1[OH:28])=[O:23])[CH:10]([CH3:12])[CH3:11])[CH3:9]

Participants

5

Reactant 3

HCID 93483-Phenylsalicylic acidHCID 10340Sodium CarbonateHCID 54447467(2,4-Dimethyl-3-pentyl) methanesulfonate

Product 1

HCID 110560652-(2,4-Dimethyl-3-pentyloxy)carbonyl-6-phenylphenolYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a four-neck flask having an inner volume of 100 ml, 4.86 g (25 m.mols) of (2,4-dimethyl-3-pentyl) methanesulfonate, 5.36 g (25 m.mols) of 3-phenylsalicylic acid, 2.65 g (25 m.mols) of sodium carbonate, and 50 ml of dimethyl formamide were placed and left reacting at 90° C. for three hours. After the reaction, the reaction mass was thrown into 100 ml of ice water and extracted twice with 150 ml of ethyl acetate. The organic layer obtained consequently was washed twice with 50 ml of water. Then, by distilling the organic layer thereby expelling the solvent by evaporation, 5.00 g (16 m.mols) of 2-(2,4-dimethyl-3-pentyloxy)carbonyl-6-phenylphenol was obtained as the product aimed at.

Workup

  1. customIn a four-neck flask having
  2. waitleft
  3. customAfter the reaction
  4. extractionextracted twice with 150 ml of ethyl acetate
  5. customThe organic layer obtained consequently
  6. washwas washed twice with 50 ml of water
  7. distillationThen, by distilling the organic layer
  8. customby evaporation

Sources & evidence

ORD record
ord-40d1a19b81ae45b9b295034e5f43b00b
Source dataset
uspto-grants-1999_12
Patent number
US05998609

Reaction notes

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