Water → Methyl 2-hydroxy-4-(3-trimethylsilanyl-propyloxy)-benzoate

HRID 843279Notes

Reaction equation

HRID 843279 reaction equation
[C:1]([O:11][CH3:12])(=[O:10])[C:2]1[C:3](=[CH:5][CH:6]=[C:7]([CH:9]=1)O)[OH:4].[C:13](=[O:16])([O-])[O-].[K+].[K+].ClC[CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24].O>CN(C=O)C>[OH:4][C:3]1[CH:5]=[C:6]([O:16][CH2:13][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:7]=[CH:9][C:2]=1[C:1]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 75077Methyl GentisateHCID 75362(3-Chloropropyl)trimethylsilane

Product 1

HCID 15383569Methyl 2-hydroxy-4-(3-trimethylsilanyl-propyloxy)-benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of methyl gentisate (16.8 g, 0.1 mole) and potassium carbonate (15.2 g, 0.11 mole) in 80 ml of DMF in a nitrogen atmosphere at 80° C. is added chloropropyl trimethyl silane (16.6 g, 0.11 mole) drop by drop over a 20-minute period. The mixture is heated to 90° C. for 8 hours. It is cooled and then poured into 200 ml of water. Extraction is performed with diisopropyl ether. The organic phase is washed with water, dried with sodium sulfate, and then concentrated. After silica chromatography of the resulting yellow oil (eluent: Heptane/CH2Cl2 90:10) we obtain 3.3 g of a clean fraction of methyl 2-hydroxy-4-(3-trimethylsilanyl-propyloxy)-benzoate.

Workup

  1. temperatureIt is cooled
  2. extractionExtraction
  3. washThe organic phase is washed with water
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-393dcca4d75a493ea9c6c2ef11dd663b
Source dataset
uspto-grants-2002_04
Patent number
US06376679B2

Reaction notes

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