Hydrochloric Acid → HCID 23282419, compound

HRID 369677Notes

Reaction equation

HRID 369677 reaction equation
[H-].[Na+].[H][H].[Cl:5][C:6](Cl)=[CH:7][CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14].Cl>CO.CN(C)C=O>[Cl:5][C:6]#[C:7][CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 23282403HCID 23282403, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23282419HCID 23282419, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

In a reaction vessel containing 10 ml of N,N-dimethylformamide and 0.088 g of 60% sodium hydride (in oil) was put 0.070 g of methanol under ice cooling, and the mixture was stirred until the evolution of hydrogen gas ceased, to which 0.40 g of 4-(3,3-dichloro-2-propenyloxy)butanol was added. After stirring at 50° C. for 3 hours, the reaction mixture was poured into diluted hydrochloric acid and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over magnesium sulfate and then concentrated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.20 g of 4-(3-chloro-2-propynyloxy)butanol (yield, 62%), nD24.6 1.4720.

Workup

  1. additionwas added
  2. extractionextracted twice with diethyl ether
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give a crude product

Sources & evidence

ORD record
ord-2649c3b2a92a4c1ab5b3f9dcb4c36071
Source dataset
uspto-grants-2000_10
Patent number
US06140274

Reaction notes

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