Ammonia → 7,11-Hexadecadiynol

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[CH:9]#[C:10][CH2:11][CH2:12][C:13]#[C:14][CH2:15][CH2:16][CH2:17][CH3:18].[Li].N>>[CH2:7]([OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:9]#[C:10][CH2:11][CH2:12][C:13]#[C:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

Reactant 3

HCID 222Ammonia

HCID 779706-Bromo-1-hexanol2×

HCID 86734238Lithium 1,5-decadiyne

Product 1

HCID 214931027,11-Hexadecadiynol

Procedure

The use of a protected derivative of 6-bromohexanol can be avoided thus an excess of lithium 1,5-decadiyne in liquid ammonia is used and allowed to react directly with 6-bromohexanol to give 7,11-hexadecadiynol (bp 136°-138°/1 torr, nD21 1.4818). Acetylation with acetic anhydride or acetic acid-acetyl chloride converts the alcohol to the acetate.

Sources & evidence

ORD record: ord-94aae238ea7b429088a03b46b1cf8840
Source dataset: uspto-grants-1976_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03996270

Reaction notes

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