Formaldehyde → (Z)-2-Tridecen-1-ol

HRID 1759600Notes

Reaction equation

HRID 1759600 reaction equation
[CH2:1]=[O:2].C([Al](CCCCCCCCCC)[CH:14]=[CH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])CCCCCCCCC>CCCCCC>[CH2:1]([OH:2])/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 57352683Aluminum, didecyl-(1E)-1-dodecenyl-

Product 1

HCID 5364998(Z)-2-Tridecen-1-olYield 21.5%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Similarly to the procedure described in Example 1, a 17% slurry of 159 grams (5.29 moles) of paraformaldehyde in n-hexane was treated with 1488 grams (3.12 moles) of di-n-decyl dodecenyl aluminum (obtained from tri-n-decyl aluminum and acetylene). Distillation of the hydrolysis product was performed under 0.35 mm Hg. The product fraction was removed at 89°-99° C. There was obtained 133 grams (0.67 moles) of cis-2-tridecen-1-ol (13.3% of theoretical yield), having a purity of 92%. Identity of the compound was confirmed by ir and nmr spectral analyses.

Workup

  1. distillationDistillation of the hydrolysis product
  2. customThe product fraction was removed at 89°-99° C

Sources & evidence

ORD record
ord-1314b716d48f4ffa92d406c9e7403df4
Source dataset
uspto-grants-1982_07
Patent number
US04341910

Reaction notes

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