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

HRID 15093

Reaction equation

HRID 15093 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-56c41f6bf0024c31984b059fda2d4356
Source dataset
uspto-grants-2010_06
Patent number
US07732471B2

Linked notes

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