Formaldehyde → HCID 53963888, compound

HRID 1414939Notes

Reaction equation

HRID 1414939 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][CH2:13][C:14]#[CH:15])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].O1[CH2:21][CH2:20]COO1.C=O.[CH2:24]([NH:26][CH2:27]C)[CH3:25]>O1CCOCC1.C(O)(=O)C>[CH2:24]([N:26]([CH2:20][CH3:21])[CH2:27][C:15]#[C:14][CH2:13][CH2:12][CH2:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:6]=1)[CH3:25]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 8021DiethylamineHCID 19593658CID 19593658HCID 54457357Phenol, 3-(4-pentyn-1-yl)-, 1-acetate

Product 1

HCID 53963888HCID 53963888, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Add 5-m-acetoxyphenylpent-1-yne (9.5 g) to a mixture of trioxan (0.5 g), 40% formalin (5.5g), diethylamine (4g), acetic acid (2.75 g), dioxan (25 cc), and cuprous chloride (0.13 g) at room temperature. Heat the mixture thus obtained to 70°, to obtain a clear green solution, and maintain under nitrogen at that temperature for 12 hours. Cool and add ice, pour the product into ice-cold saturated potassium bicarbonate and extract the mixture with ether. Wash and dry, evaporate the extracts under reduced pressure and distil to obtain 1-diethylamino-6-m-acetoxyphenylhex-2-yne (9.9 g), b.p. 152°-154°/0.1 mm, as a pale yellow mobile liquid.

Workup

  1. temperatureHeat the mixture
  2. customthus obtained to 70°
  3. customto obtain a clear green solution
  4. temperaturemaintain under nitrogen at that temperature for 12 hours
  5. temperatureCool
  6. additionadd ice
  7. additionpour the product into ice-cold saturated potassium bicarbonate
  8. extractionextract the mixture with ether
  9. washWash
  10. customdry
  11. customevaporate the extracts under reduced pressure
  12. customdistil

Sources & evidence

ORD record
ord-8b57c8643bb64731bda46cdf55d7f49b
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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