Formaldehyde → 1-Diethylamino-6-(3,4-dimethoxyphenyl)hex-2-yne

HRID 1414941Notes

Reaction equation

HRID 1414941 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH2:13][C:14]#[CH:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O1[CH2:21][CH2:20]COO1.C=O.[CH2:24]([NH:26][CH2:27]C)[CH3:25].[OH-].[Na+]>O1CCOCC1.C(O)(=O)C.O>[CH2:24]([N:26]([CH2:20][CH3:21])[CH2:27][C:15]#[C:14][CH2:13][CH2:12][CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:25]

Participants

9

Reactant 5

HCID 712FormaldehydeHCID 8021DiethylamineHCID 14798Sodium HydroxideHCID 19593658CID 19593658HCID 214858375-(3,4-Dimethoxyphenyl)-pent-1-yne

Product 1

HCID 214857251-Diethylamino-6-(3,4-dimethoxyphenyl)hex-2-yne

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Heat a mixture of 5-(3,4-dimethoxyphenyl)-pent-1-yne (8 g), water (2.5 cc), trioxan (0.5 g ), 30% formalin (5.5 g), diethylamine (4 g), acetic acid (2.75 g), dioxan (25 cc) and cuprous chloride (0.13 g) at 70° for 15 hours. Make the cooled solution alkaline with 10% aqueous sodium hydroxide and collect the product. Wash the ethereal solution with water and extract with 10% hydrochloric acid (3 × 30 cc). Wash the combined aqueous extracts with ether, make it alkaline with 10% sodium hydroxide solution and extract with ether. Wash and dry the ethereal solution, evaporate the solvent and distil the residue at 0.1 mm Hg to obtain 1-diethylamino-6-(3,4-dimethoxyphenyl)-hex-2-yne.

Workup

  1. temperatureHeat
  2. customcollect the product
  3. washWash the ethereal solution with water
  4. extractionextract with 10% hydrochloric acid (3 × 30 cc)
  5. washWash the combined aqueous extracts with ether
  6. extractionextract with ether
  7. washWash
  8. customdry the ethereal solution
  9. customevaporate the solvent
  10. customdistil the residue at 0.1 mm Hg

Sources & evidence

ORD record
ord-48bbbec8e91840ae901612f74f490c37
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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