Phenol → HCID 13290150, compound

HRID 1680034Notes

Reaction equation

HRID 1680034 reaction equation
C(Cl)(=O)C(C)(C)C.[CH3:8]/[C:9](=[CH:13]\[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[CH:16][CH:15]=1)/[C:10]([OH:12])=[O:11].C(N(CC)CC)C.[C:34]1(O)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)Cl.N1C=CC=CC=1>[C:34]1([O:11][C:10](=[O:12])/[C:9](/[CH3:8])=[CH:13]/[C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[CH:16][CH:15]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 6437388(2E)-2-Methyl-3-[4-(3-pyridinylmethyl)phenyl]acrylic acid

Product 1

HCID 13290150HCID 13290150, compoundYield 60.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 105 mg of pivaloyl chloride in one ml of methylene chloride was added to a solution of 200 mg of the acrylic acid(prepared as described in Example 15) and 0.1257 ml of triethylamine in 5 ml of methylene chloride at room temperature, and the mixture was stirred at room temperature for one hour. To it were added 1.47 g of phenol and 1.323 ml of pyridine, the mixture was stirred overnight at room temperature, and concentrated under reduced pressure. The residue was dissolved in diethyl ether, washed with a saturated aqueous solution of sodium bicarbonate, and a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (3:2) as eluent to give 158 mg of the title compound having the following physical characteristics:

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in diethyl ether
  4. washwashed with a saturated aqueous solution of sodium bicarbonate
  5. dry with materiala saturated aqueous solution of sodium chloride, dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel using
  8. additiona mixture of cyclohexane and ethyl acetate (3:2) as eluent

Sources & evidence

ORD record
ord-36741ea874024d3b925a8a11b66324ee
Source dataset
uspto-grants-1981_06
Patent number
US04271170

Reaction notes

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