1-Butanol → HCID 54296778, compound

HRID 620946Notes

Reaction equation

HRID 620946 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].[H-].[Na+].Br[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16](=[CH:21][O:22][CH3:23])[C:17]([O:19][CH3:20])=[O:18].[Na+].[Cl-]>CN(C)C=O.C1COCC1>[CH2:1]([O:5][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16](=[CH:21][O:22][CH3:23])[C:17]([O:19][CH3:20])=[O:18])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 2631-ButanolHCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 53395349Methyl 2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoate

Product 1

HCID 54296778HCID 54296778, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

7.4 g of n-butanol are dissolved in 50 ml of dimethylformamide, and 2.4 g of sodium hydride are added. The solution is slightly heated until everything has reacted. This solution is gradually added dropwise at -20° C. to 28.4 g of methyl α-(2-bromomethylphenyl)-β-methoxyacrylate in 150 ml of THF. Once the bromomethyl compound is no longer detectable by thin layer chromatography, 100 g of ice and 100 ml of saturated NaCl solution are added. Extraction with methylene chloride gives 23 g of an oil which is chromatographed. 10 g of a resin are obtained after elution with ethyl acetate/hexane.

Workup

  1. temperatureThe solution is slightly heated until everything
  2. customhas reacted
  3. additionare added
  4. extractionExtraction with methylene chloride

Sources & evidence

ORD record
ord-4f300ecd93af47628214ca8e67ada25f
Source dataset
uspto-grants-1989_04
Patent number
US04822908

Reaction notes

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