Potassium → HCID 20570483, compound

HRID 1577958Notes

Reaction equation

HRID 1577958 reaction equation
[K].[Cl:2][C:3]1([Cl:13])[CH2:8][CH:7]2[C:9]([CH3:11])([CH3:10])[C:4]1([CH3:12])[CH2:5][CH2:6]2>>[Cl:2][C:3]1([Cl:13])[CH2:8][CH:7]2[C:9]([CH3:10])([CH3:11])[C:4]1([CH3:12])[CH2:5][CH2:6]2.[C:4]12([CH3:12])[C:9]([CH3:11])([CH3:10])[C:7](=[CH:6][CH2:5]1)[CH:8]=[CH:3]2

Participants

4

Reactant 2

HCID 5462222PotassiumHCID 20570483HCID 20570483, compound

Product 2

HCID 20570483HCID 20570483, compoundHCID 23036804HCID 23036804, compound

Conditions

Temperature
197 °C

Procedure

A 3-neck 100 ml flask was charged with 50 ml of cis-pinanol. 1.4 g (0.036 g atoms) of potassium metal was added and the flask was brought to reflux at 197° C. with stirring under nitrogen. When alkoxide formation was complete, 3.5 g (16.7 mmoles) dichlorocamphane was added to the reaction. Using gas chromatography, conversions were calculated with cis-pinanol as the internal standard. The use of cis-PinanOK gave nearly complete conversion of dichlorocamphane to bornadiene in 12 minutes. This is in sharp contrast to no conversion or very difficult conversions reported in previous references. Results are given in Table 4.

Sources & evidence

ORD record
ord-465c07e06f764aa8a08920e90396ec42
Source dataset
uspto-grants-1981_09
Patent number
US04289917

Reaction notes

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