Benzoic acid, 2-hydroxy-3-methyl-, methyl ester → HCID 22922977, compound

HRID 2257449Notes

Reaction equation

HRID 2257449 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].O[C:9]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:19][C:18]1[C:9]([C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 2

HCID 31835Benzoic acid, 2-hydroxy-3-methyl-, methyl esterHCID 62493Pivaloyl chloride

Product 1

HCID 22922977HCID 22922977, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Pivaloyl chloride is added dropwise at 10°-15° C. to a stirred mixture of methyl 2-hydroxy-3-methylbenzoate and 4-dimethylaminopyridine in 25 ml of dichloromethane. After 2 hours at room temperature, the reaction is quenched with 200 ml of water. The organic layer is washed with 5% sodium bicarbonate, dried on anhydrous sodium sulfate and evaporated in vacuo. The product is purified by flash chromatography on silica gel.

Workup

  1. customthe reaction is quenched with 200 ml of water
  2. washThe organic layer is washed with 5% sodium bicarbonate
  3. dry with materialdried on anhydrous sodium sulfate
  4. customevaporated in vacuo
  5. customThe product is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-cc171b570c694c5092f95537272df1a8
Source dataset
uspto-grants-1997_08
Patent number
US05658587

Reaction notes

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