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

HRID 2049207

Reaction equation

HRID 2049207 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-2d6780dfe1b148b5b4f822b6054aec71
Source dataset
uspto-grants-1980_04
Patent number
US04197258

Linked notes

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