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

HRID 26176
Notes
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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]
ParticipantsConditionsProcedureSources & evidenceReaction notes

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

On this pageParticipantsConditionsProcedureSources & evidenceReaction notes
HCID 24462
Copper Sulfate
Catalyst
HCID 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04148824

Reaction notes

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