Formaldehyde → HCID 21485425, compound

HRID 1414938Notes

Reaction equation

HRID 1414938 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]#[CH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1[CH2:17][CH2:16]COO1.C=O.[CH2:20]([NH:22][CH2:23]C)[CH3:21].[OH-].[Na+]>O1CCOCC1.C(O)(=O)C.O>[CH2:20]([N:22]([CH2:16][CH3:17])[CH2:23][C:11]#[C:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:21]

Participants

9

Reactant 5

HCID 712FormaldehydeHCID 8021DiethylamineHCID 14798Sodium HydroxideHCID 745735-Phenyl-1-pentyneHCID 19593658CID 19593658

Product 1

HCID 21485425HCID 21485425, compoundYield 886.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Maintain 5-phenylpent-1-yne (20 g) for 12 hours at 70° under nitrogen with water (6.2 cc), trioxan (1.2 g), 30% formalin (13.8 g), diethylamine (10 g), acetic acid (6.9 g), dioxan (62 cc) and cuprous chloride (0.35 g). Make the cooled solution alkaline with sodium hydroxide. Extract with ether and extract the ether extract itself with hydrochloric acid. Make the purified aqueous hydrochloride solution thus obtained alkaline again and extract with ether. Dry, evaporate the ether extract and distil the residue to obtain 1-diethylamino-6-phenylhex-2-yne (27.1 g), b.p. 104°-106°/0.2 mm.

Workup

  1. extractionExtract with ether
  2. extractionextract the ether
  3. extractionextract itself with hydrochloric acid
  4. extractionextract with ether
  5. customDry
  6. customevaporate the ether
  7. extractionextract
  8. customdistil the residue

Sources & evidence

ORD record
ord-aa43cb0791e14b69b0bafcc88b8e1583
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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