1-Octanol → 2(Octyloxy)methylbromobenzene

HRID 1639211Notes

Reaction equation

HRID 1639211 reaction equation
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C([Li])CCC.[Br:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18]Br>O1CCCC1.C(N(C)C)=O.CCCCCC>[CH2:1]([O:9][CH2:18][C:17]1[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=1[Br:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 9571-OctanolHCID 769652-Bromobenzyl bromideHCID 178418339Butyllithium

Product 1

HCID 146763902(Octyloxy)methylbromobenzene

Reagents, catalysts & solvents 1

HCID 86741340Tetrahydrofuran hexane dimethyl formamideSolvent

Procedure

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 dichloro methane/hexane mixture).

Sources & evidence

ORD record
ord-283df81ed10843f79ee322b827c83975
Source dataset
uspto-grants-1989_11
Patent number
US04883614

Reaction notes

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