Sodium hydride → Methyl 2-methyl-2-(8-nonenyloxy)propionate

HRID 857203Notes

Reaction equation

HRID 857203 reaction equation
[H-].[Na+].[OH:3][C:4]([CH3:10])([CH3:9])[C:5]([O:7][CH3:8])=[O:6].Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]=[CH2:20]>CN(C)C=O>[CH3:9][C:4]([O:3][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=[CH2:12])([CH3:10])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75024Methyl alpha-hydroxyisobutyrateHCID 110199989-Bromo-1-nonene

Product 1

HCID 21866680Methyl 2-methyl-2-(8-nonenyloxy)propionateYield 30.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 500 ml of dry N,N-dimethylformamide, 17 g of 60% sodium hydride was added, and 48 g of methyl 2-hydroxyisobutyrate was added dropwise with stirring under ice-cooling, and stirred for 10 minutes. Then, 100 g of 9-bromo-1-nonene (purity: 63.4%) was added, and the mixture was stirred for 15 hours at room temperature. The reaction solution was poured into ice-cold water, extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was distilled under reduced pressure to give 29.9 g of the objective compound as yellowish oil.

Workup

  1. temperaturecooling
  2. stirringstirred for 10 minutes
  3. stirringthe mixture was stirred for 15 hours at room temperature
  4. additionThe reaction solution was poured into ice-cold water
  5. extractionextracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-6c94b13272df470184644055bfa721f0
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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