Formaldehyde → 4-(Diethylamino)-2-butyn-1-ol

HRID 26176

Reaction equation

HRID 26176 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].[CH2:5]=O.[CH2:7]([NH:9][CH2:10][CH3:11])[CH3:8].[I-].[K+].S(=O)(=O)(O)O>S([O-])([O-])(=O)=O.[Cu+2].O>[CH2:7]([N:9]([CH2:10][CH3:11])[CH2:5][C:3]#[C:2][CH2:1][OH:4])[CH3:8]

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 7859Propargyl alcoholHCID 8021Diethylamine

Product 1

HCID 827354-(Diethylamino)-2-butyn-1-olYield 86%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent

Conditions

Temperature
92 °C

Procedure

204 parts by weight of aqueous 55% strength propargyl alcohol, 250 parts by weight of 30% strength aqueous formaldehyde, 161 parts by weight of diethylamine, 1.4 parts by weight of copper sulfate, 2 parts by weight of potassium iodide, 50 parts by weight of water and 115 parts by weight of concentrated sulfuric acid are mixed and brought to pH 5. The mixture is heated for 5 hours at 92° C. and worked up as described. 242 parts by weight of 1-diethylaminobut-2-yn-4-ol are obtained, corresponding to a yield of 86%.

Sources & evidence

ORD record
ord-947d44843c3f4b7fbab1d2263be8b0ed
Source dataset
uspto-grants-1979_04
Patent number
US04148824

Linked notes

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