Water → Tert-butyl 2-(3-hydroxypropoxymethyl)-6-methylbenzoate

HRID 15093

Reaktionsgleichung

Reaktionsgleichung von HRID 15093
[CH:1]([OH:5])(O)[CH2:2][CH3:3].[H-].[Na+].Br[CH2:9][C:10]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:11]=1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[OH2:24]>CN(C=O)C>[OH:24][CH2:3][CH2:2][CH2:1][O:5][CH2:9][C:10]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:11]=1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 134919PropanediolHCID 59341261tert-Butyl 2-(bromomethyl)-6-methylbenzoate

Produkt 1

HCID 59341259Tert-butyl 2-(3-hydroxypropoxymethyl)-6-methylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

25.5 ml of propane diol are slowly added dropwise at RT to a suspension of 3.37 g of sodium hydride (60% by weight in mineral oil) in 400 ml of DMF. After gas evolution ceases, 20 g of tert-butyl 2-bromomethyl-6-methylbenzoate are added, and the solution is stirred at RT for 72 h. Water is added and the solution is extracted twice with MTBE, and the org. phases are combined, washed with water and sat. NaCl solution, dried over MgSO4 and concentrated. The residue is chromatographed on silica gel with a heptane/ethyl acetate gradient, resulting in 16 g of tert-butyl 2-(3-hydroxypropoxymethyl)-6-methylbenzoate as a colorless oil.

Aufarbeitung

  1. extractionthe solution is extracted twice with MTBE
  2. washwashed with water and sat. NaCl solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel with a heptane/ethyl acetate gradient
  6. customresulting in 16 g of tert-butyl 2-(3-hydroxypropoxymethyl)-6-methylbenzoate as a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-56c41f6bf0024c31984b059fda2d4356
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732471B2

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