1-Octanol → 2(Octyloxy)methylbromobenzene

HRID 330114Notes

Reaction equation

HRID 330114 reaction equation
[C:1]([O-:10])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Li+].C(O)CCCCCCC.C([Li])CCC.[Br:26][C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[CH2:29]Br>O1CCCC1.C(N(C)C)=O.CCCCCC>[CH2:1]([O:10][CH2:29][C:28]1[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=1[Br:26])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 9571-OctanolHCID 769652-Bromobenzyl bromideHCID 23673717Octanoic acid, lithium salt (1:1)HCID 178418339Butyllithium

Product 1

HCID 146763902(Octyloxy)methylbromobenzene

Reagents, catalysts & solvents 1

HCID 86741340Tetrahydrofuran hexane dimethyl formamideSolvent

Procedure

Lithium octanoate, prepared from octanol and n-butyllithium, in a mixture of tetrahydrofuran/hexane dimethyl formamide was condensed with 2-bromobenzyl bromide to yield 2(octyloxy)methylbromobenzene. This material was treated with n-butyllithium in ether/hexane mixture and subsequently treated with paraformaldehyde to yield 2-(octyloxy)methylbenzyl alcohol. This material was then treated with triphenyl phosphonine bromide to yield [[2-[(octyloxy)-methyl]phenyl]methyl]triphenyl phosphonium bromide. Condensation of this material with 7-formyl-3-methyl-2,4,6-octatrienoic acid ethyl ester, as in Example 3, followed by hydrolysis, as in Example 5, gave the (All-E)-3,7-Dimethyl-9-[2-[(octyloxy)-methyl]phenyl]-2,4,6,8-nonatetraenoic acid, mp 120°-121° (from methane/hexane mixture).

Sources & evidence

ORD record
ord-920b6432243646e2a7175ff5fef90c40
Source dataset
uspto-grants-1990_01
Patent number
US04894480

Reaction notes

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