Water → HCID 21829738, compound

HRID 1600484Notes

Reaction equation

HRID 1600484 reaction equation
[C:1]([O:11][CH3:12])(=[O:10])[C:2]1[C:3](=[CH:5][CH:6]=[C:7]([CH:9]=1)[OH:8])[OH:4].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24].O>CN(C=O)C>[OH:4][C:3]1[CH:5]=[CH:6][C:7]([O:8][CH2:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])=[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 21829738HCID 21829738, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of methyl gentisate (16.8 g, 0.1 mol) and potassium carbonate (15.2 g, 0.11 mol) in 80 ml of DMF, under a nitrogen atmosphere at 80° C., was added chloropropyltrimethylsilane (16.6 g, 0.11 mol) dropwise over 20 minutes. The mixture was heated at 90° C. for 8 hours. It was cooled and poured into 200 ml of water. The mixture was extracted with diisopropyl ether. The organic phase was washed with water, dried over sodium sulphate and then concentrated. After chromatography on silica of the yellow oil obtained (eluent: 90/10 heptane/CH2Cl2), 3.3 g of a clean fraction of methyl 2-hydroxy-5-(3-trimethylsilanylpropyloxy)benzoate were recovered.

Workup

  1. temperatureIt was cooled
  2. extractionThe mixture was extracted with diisopropyl ether
  3. washThe organic phase was washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f2362c37213442fd9ccaa166de30e479
Source dataset
uspto-grants-1999_11
Patent number
US05976558

Reaction notes

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