Formaldehyde → 2-Tetradecynol

HRID 1612797Notes

Reaction equation

HRID 1612797 reaction equation
[CH2:1]([OH:13])[C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH:14]#[C:15]CCCCCCCCCCC.[Li]CCCC.C=O>CCOCC>[CH2:1]([OH:13])[C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1177541-TridecyneHCID 1712322Dodec-2-yn-1-olHCID 178418339Butyllithium

Product 1

HCID 109657922-Tetradecynol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-Tetradecyn-1-ol was prepared as described above for 2-dodecyn-1-ol except that 5.0 g (27 mmole) of 1-tridecyne in 200 ml of ether, 11.6 ml (29 mmole) of n-BuLi, and 874 mg (29 mmole) of paraformaldehyde was used. The reaction afforded a white solid after workup which was crystallized from petroleum ether to yield 4.78 g of white crystals, mp 44°-6° C. 1H NMR δ4.25 (m, 2), 2.20 (m, 2), 1.6-1.2 (m, 20), 0.88 (t, 3, J=7 Hz).

Workup

  1. customThe reaction afforded a white solid after workup which
  2. customwas crystallized from petroleum ether

Sources & evidence

ORD record
ord-424fbd23b1ac45e19d8a9ca2fbc8cea8
Source dataset
uspto-grants-1993_03
Patent number
US05190969

Reaction notes

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