7131. 1-Pentol

Nomenclature

CAS number: 105-29-3
3-Methyl-2-penten-4-yn-1-ol; 1-hydroxy-3-methyl-2-penten-4-yne.
C6H8O; mol wt 96.13.
C 74.97%, H 8.39%, O 16.64%.

Description and references

Prepd by allylic rearrangement of methylvinylethynyl carbinol with moderately strong acid at 80°: Oroshnik, J. Am. Chem. Soc. 78, 2651 (1956).

Chemical structure

Derivative

cis-Form.

Nomenclature

1′-Pentol.

Properties

Oily liquid. bp9.4 65°. nD20 1.4820. uv max (ethanol): 223 nm (ε 11,000).

Derivative

cis-Form p-nitrobenzoate.

Properties

mp 61-62°.

Derivative

trans-Form.

Nomenclature

1″-Pentol.

Properties

Oily liquid. bp9.4 73°. nD20 1.4934. uv max (ethanol): 224 nm (ε 13,100).

Derivative

trans-Form p-nitrobenzoate.

Properties

mp 63-64°.

Caution

Both isomers tend to polymerize and will explode when heated above 120° in a sealed bomb tube.

Use

Intermediate in vitamin A synthesis.