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

HRID 1895559

Reaction equation

HRID 1895559 reaction equation
[CH2:1]=O.[CH2:3]([NH:5][CH2:6][CH3:7])[CH3:4].[CH2:8]([OH:11])[C:9]#[CH:10]>O1CCOCC1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:3]([N:5]([CH2:6][CH3:7])[CH2:1][C:10]#[C:9][CH2:8][OH:11])[CH3:4]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 7859Propargyl alcoholHCID 8021Diethylamine

Product 1

HCID 827354-(Diethylamino)-2-butyn-1-olYield 84%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
62.5 °C

Procedure

A mixture of para formaldehyde (105.0 g), N,N-diethyl amine (300 g) and copper(II) acetate (7.5 g) in 1,4 dioxane (900 ml) was heated to 60-65° C. After 1.5 h, 2-propyne-1-ol (150 g, 2.7 moles) was added and the mixture was heated at 90-95° C. after 2 hrs; excess solvent, 1,4 dioxane, evaporated at reduced pressure to afford 315 g (84%) of the product as an oil.

Workup

  1. temperaturethe mixture was heated at 90-95° C. after 2 hrs
  2. customexcess solvent, 1,4 dioxane, evaporated at reduced pressure

Sources & evidence

ORD record
ord-5907d465b5074e328cd79f96e5ebc09f
Source dataset
uspto-grants-2013_08
Patent number
US08513455B2

Linked notes

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