Formaldehyde → HCID 20327682, compound

HRID 372514Notes

Reaction equation

HRID 372514 reaction equation
[C:1]([O:4][C:5]([CH2:11][CH2:12][CH3:13])([CH2:8][CH2:9][CH3:10])[C:6]#[CH:7])(=[O:3])[CH3:2].[CH2:14]([NH:16][CH2:17][CH3:18])[CH3:15].C=O.O1CCOC[CH2:22]1>CCOCC>[CH2:14]([N:16]([CH2:17][CH3:18])[CH2:22][C:7]#[C:6][C:5]([O:4][C:1](=[O:3])[CH3:2])([CH2:8][CH2:9][CH3:10])[CH2:11][CH2:12][CH3:13])[CH3:15]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8021DiethylamineHCID 312751,4-DioxaneHCID 20327651HCID 20327651, compound

Product 1

HCID 20327682HCID 20327682, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3-acetoxy-3-propyl-1-hexyne (115.2 g., 0.634 mole), diethylamine (51 g., 0.7 mole), paraformaldehyde (24.9 g., 0.83 mole) and dioxane (120 ml.) is stirred and heated on the steam bath for 2 hours. The reaction mixture is cooled, treated with ether and the product extracted into ice-cold 5% hydrochloric acid. The cold acidic solution is then basified with ice-cold 10% sodium hydroxide. The oily amine is taken up in ether, washed with water and brine and dried over sodium sulfate. Distillation yields 99.5 g. (59%) of the amine product, b.p. 101°-110° C./0.1 mm.

Workup

  1. temperatureheated on the steam bath for 2 hours
  2. temperatureThe reaction mixture is cooled
  3. extractionthe product extracted into ice-cold 5% hydrochloric acid
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. distillationDistillation
  7. customyields 99.5 g

Sources & evidence

ORD record
ord-8a92269fbf414beea2e8a87d9bb49bf9
Source dataset
uspto-grants-1978_05
Patent number
US04091107

Reaction notes

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