1,6-Dibromohexane → 1-[4-[(6-Bromohexyl)oxy]butyl]benzene

HRID 2308413Notes

Reaction equation

HRID 2308413 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.[OH-].[K+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 123681,6-DibromohexaneHCID 14797Potassium HydroxideHCID 76889Benzenebutanol

Product 1

HCID 110124391-[4-[(6-Bromohexyl)oxy]butyl]benzene

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent2×

Procedure

At a temperature between 20 and 25° C., with stirring, a mixture of 247.5 ml (1.65 mol) of 4-phenylbutanol and 500 ml of toluene are added within 45 minutes to a mixture of 509.6 ml (3.3 mol) of 1,6-dibromohexane, 402 g of powdered (6.1 mol KOH) caustic potash, 5.6 g (0.165 mol) tetra-n-butylammonium hydrogen sulphate and 1250 ml of toluene.

Sources & evidence

ORD record
ord-770c18dbbf1642cc8e2ab725a7e65b23
Source dataset
uspto-grants-2004_12
Patent number
US06835857B2

Reaction notes

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