Ammonia → HCID 14284973, compound

HRID 1973171Notes

Reaction equation

HRID 1973171 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]/[CH:13]=[CH: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]/[CH:13]=[CH:14]/[CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 779706-Bromo-1-hexanol2×HCID 86734239HCID 86734239, compound

Product 1

HCID 14284973HCID 14284973, compound

Procedure

The use of a protected derivative of 6-bromohexanol can be avoided. Thus, an excess of lithium (E)-5-decen-1-yne in liquid ammonia is used and allowed to react directly with 6-bromohexanol to give (E)-11-hexadecen-7-yne-1-ol, bp 134°-136°/1 mm, nD21 1,4755. Acetylation converts the alcohol to the above acetate.

Sources & evidence

ORD record
ord-d70a888edb6d485487bbc5bfcaf9cf88
Source dataset
uspto-grants-1976_12
Patent number
US03996270

Reaction notes

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