Formaldehyde → Butylidynetrimethanol

HRID 46725

Reaction equation

HRID 46725 reaction equation
[CH2:1]=[O:2].[OH-:3].[Na+].[CH:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9].[C:11](#N)C>>[CH2:7]([C:6]([CH2:5][OH:10])([CH2:11][OH:3])[CH2:1][OH:2])[CH2:8][CH3:9]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 6342AcetonitrileHCID 8063Pentanal2×HCID 14798Sodium Hydroxide

Product 1

HCID 81928Butylidynetrimethanol

Conditions

Temperature
80 °C

Procedure

To a heated (ca. 60° C.), rapidly stirred mixture of 9.9 grams (0.33 mole) of para-formaldehyde, 4.8 grams (0.12 mole) of finely pulverized, anhydrous sodium hydroxide, and 100 mls. of acetonitrile, was added, drop-wise, 8.4 grams of valeraldehyde. After drop-wise addition of the valeraldehyde had been completed, the reaction mixture was maintained at 80° C. for a period of 1/2 hour. At this time, 8.4 grams of insoluble solid (sodium formate and excess para-formaldehyde) was removed by filtration and discarded. Removal of the actonitrile solvent left 13.3 grams (88%) of a viscous oil which was identified as the title compound, B.P. ca. 140° C.-155° C./0.4 mm Hg.; recrystallized from a chloroform-acetonitrile mixed solvent, m.p. 100°-101° C.

Workup

  1. temperatureTo a heated
  2. customAt this time, 8.4 grams of insoluble solid (sodium formate and excess para-formaldehyde) was removed by filtration
  3. customRemoval of the actonitrile solvent
  4. waitleft 13.3 grams (88%) of a viscous oil which
  5. customrecrystallized from a chloroform-acetonitrile mixed solvent, m.p. 100°-101° C.

Sources & evidence

ORD record
ord-5f3a7df1d5374d2e9a767f259cc1673d
Source dataset
uspto-grants-1979_11
Patent number
US04175053

Linked notes

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