Formaldehyde → 1-Diethylamino-6-(m-methoxyphenyl)hept-2-yne

HRID 1077126Notes

Reaction equation

HRID 1077126 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]([CH3:14])[CH2:10][CH2:11][C:12]#[CH:13])[CH:6]=[CH:7][CH:8]=1.[CH2:15]=O.[CH2:17]([NH:19][CH2:20][CH3:21])[CH3:18].[OH-].[Na+]>O1CCOCC1.C(O)(=O)C.O>[CH2:17]([N:19]([CH2:20][CH3:21])[CH2:15][C:13]#[C:12][CH2:11][CH2:10][CH:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:14])[CH3:18]

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 8021DiethylamineHCID 14798Sodium HydroxideHCID 214858185-(3-Methoxyphenyl)-hex-1-yne

Product 1

HCID 214856761-Diethylamino-6-(m-methoxyphenyl)hept-2-yne

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Heat a mixture of 5-(3-methoxyphenyl)-hex-1-yne (56.6 g), water (17.5 cc.), 40% formalin (38.5 cc), diethylamine (40 cc), acetic acid (19 cc), dioxan (175 cc) and cuprous chloride (1 g) at 70° for 16 hours in an atmosphere of nitrogen. Make the cooled solution alkaline with 10% aqueous sodium hydroxide and extract twice with ether. Wash the ether extracts with water, filter and extract with 4N hydrochloric acid (3 × 350 cc). Make the acid extracts alkaline with 10% aqueous sodium hydroxide, extract with ether and wash the organic solution with water, brine and dry. Evaporate the solvent and distil the residue to obtain 1-diethylamino-6-(3-methoxyphenyl)-hept-2-yne, 79.5 g, b.p. 135°-140°/0.2 mm Hg nD25 1.5116.

Workup

  1. temperatureHeat
  2. extractionextract twice with ether
  3. washWash the ether
  4. filtrationfilter
  5. extractionextract with 4N hydrochloric acid (3 × 350 cc)
  6. extractionextract with ether
  7. washwash the organic solution with water, brine
  8. customdry
  9. customEvaporate the solvent
  10. customdistil the residue

Sources & evidence

ORD record
ord-e284bdaa6138487ab6d6d01ca09ab4fb
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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