Propargyl alcohol → HCID 86668669, compound

HRID 2167153Notes

Reaction equation

HRID 2167153 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].[CH3:5][O:6][C:7](=[CH:9][CH3:10])[CH3:8]>P(=O)(O)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:5][O:6][C:7]([O:4][CH2:1][C:2]#[CH:3])([CH2:9][CH3:10])[CH3:8]

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 1112062-Methoxy-2-butene

Product 1

HCID 86668669HCID 86668669, compoundYield 102.2%

Reagents, catalysts & solvents 2

HCID 1004Phosphoric AcidCatalystHCID 10340Sodium CarbonateCatalyst

Procedure

A mixture of 130 mg (0.3 μmol) of phosphoric acid (19% w/w in acetone) and 22.80 g (399 mmol) of propargyl alcohol is filled into a dropping funnel. 53.5 g (598 mmol) of 2-methoxy-but-2-ene (96.2% GC) was transferred into a second dropping funnel. Both solutions were added simultaneously within 30 minutes to the cooled flask (8° C.). The internal temperature was maintained between 8° C. and 12° C. during the addition of the reactants. The reaction mixture was held at 10° C. for about 2 hours. The reaction mixture was neutralized with 0.5 g of sodium carbonate and concentrated under reduced pressure (40° C., 80 mbar). The crude product was analyzed by GC. 58.0 g of crude 2-methoxy-2-prop-2-ynyloxy-butane were obtained with a purity of 85.5% (yield 96.9% based on propargyl alcohol).

Workup

  1. additionis filled into a dropping funnel
  2. additionBoth solutions were added simultaneously within 30 minutes to the cooled flask (8° C.)
  3. temperatureThe internal temperature was maintained between 8° C. and 12° C. during the addition of the reactants
  4. concentrationconcentrated under reduced pressure (40° C., 80 mbar)

Sources & evidence

ORD record
ord-de66f67235a7402ab111fa9e4e75b17c
Source dataset
uspto-grants-2015_06
Patent number
US09045404B2

Reaction notes

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