Formaldehyde → 1-Diethylamino-6-m-methoxyphenylhex-2-yne

HRID 1414936Notes

Reaction equation

HRID 1414936 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][C:12]#[CH:13])[CH:6]=[CH:7][CH:8]=1.O1[CH2:19][CH2:18]COO1.C=O.[CH2:22]([NH:24][CH2:25]C)[CH3:23].[OH-].[Na+]>O1CCOCC1.C(O)(=O)C.O>[CH2:22]([N:24]([CH2:18][CH3:19])[CH2:25][C:13]#[C:12][CH2:11][CH2:10][CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:23]

Participants

9

Reactant 5

HCID 712FormaldehydeHCID 8021DiethylamineHCID 14798Sodium HydroxideHCID 19593658CID 19593658HCID 212214055-m-Methoxyphenylpent-1-yne

Product 1

HCID 214855971-Diethylamino-6-m-methoxyphenylhex-2-yneYield 736.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Allow 5 -m-methoxyphenylpent-1-yne (8 g.) to stand for 12 hours at 70° C under nitrogen with 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). Make the cooled solution alkaline with 10% aqueous sodium hydroxide and extract with ether; then extract the ether extract with 10% hydrochloric acid: wash the acid extract with ether, make alkaline with 10% aqueous sodium hydroxide, extract with ether, and then wash and dry the ether extract. Distil to obtain 1-diethylamino-6-m-methoxyphenylhex-2-yne (10.6 g. 88%), b.p. 130°-131° C/0.1 mm.

Workup

  1. extractionextract with ether
  2. extractionthen extract the ether
  3. extractionextract with 10% hydrochloric acid
  4. washwash the acid
  5. extractionextract with ether
  6. extractionextract with ether
  7. washwash
  8. dry with materialdry the ether
  9. extractionextract
  10. customDistil

Sources & evidence

ORD record
ord-603744cb5b5147b2bb33041fd19e563d
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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