Formaldehyde → 1-Diethylamino-5-methyl-6-(m-methoxyphenyl)hex-2-yne

HRID 1077127Notes

Reaction equation

HRID 1077127 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([CH3:14])[CH2:11][C:12]#[CH:13])[CH:6]=[CH:7][CH:8]=1.O1[CH2:20][CH2:19]COO1.C=O.[CH2:23]([NH:25][CH2:26]C)[CH3:24].[OH-].[Na+]>O1CCOCC1.C(O)(=O)C>[CH2:23]([N:25]([CH2:19][CH3:20])[CH2:26][C:13]#[C:12][CH2:11][CH:10]([CH3:14])[CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:24]

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 8021DiethylamineHCID 14798Sodium HydroxideHCID 19593658CID 19593658HCID 214857465-(m-Methoxyphenyl)-4-methyl-pent-1-yne

Product 1

HCID 214854231-Diethylamino-5-methyl-6-(m-methoxyphenyl)hex-2-yne

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Heat 5-(m-methoxyphenyl)-4-methyl-pent-1-yne (8 g), trioxan (0.5 g), 30% formalin (5.5 cc), diethylamine (4 g), acetic acid (2.75 g), dioxan (25 cc) and cuprous chloride (0.12 g) together at 70° for 15 hours. Make cooled solution alkaline with 10% aqueous sodium hydroxide and extract with ether. Wash the ethereal solution with water and extract with 10% hydrochloric acid (3 × 20 cc). Combine the acid extracts, wash with ether and make alkaline with 10% aqueous sodium hydroxide and extract with ether. Wash the ethereal solution, dry, remove the solvent and distil the residue at 0.1 mm to obtain 1-diethylamino-5-methyl-6-(m-methoxyphenyl)-hex-2-yne.

Workup

  1. extractionextract with ether
  2. washWash the ethereal solution with water
  3. extractionextract with 10% hydrochloric acid (3 × 20 cc)
  4. washCombine the acid extracts, wash with ether
  5. extractionextract with ether
  6. washWash the ethereal solution
  7. customdry
  8. customremove the solvent
  9. customdistil the residue at 0.1 mm

Sources & evidence

ORD record
ord-34a146ef3e4c4260bbfcf3faf9846c68
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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