Formaldehyde → HCID 21485425, compound

HRID 1077123Notes

Reaction equation

HRID 1077123 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 extracts 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 extracts
  7. customdistil the residue

Sources & evidence

ORD record
ord-ce6a41f683da46269b8ccdfc072505a7
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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