1,3-Dibromopropane → 1-(3-Bromopropoxy)-2-propylbenzene

HRID 1383142Notes

Reaction equation

HRID 1383142 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])[CH2:2][CH3:3].[OH-].[Na+].[Br:13][CH2:14][CH2:15][CH2:16]Br>C(Cl)Cl.O.S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:13][CH2:14][CH2:15][CH2:16][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:1][CH2:2][CH3:3]

Participants

7

Reactant 3

HCID 80011,3-DibromopropaneHCID 125702-PropylphenolHCID 14798Sodium Hydroxide

Product 1

HCID 123558641-(3-Bromopropoxy)-2-propylbenzene

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure of Example 7 using 2-n-propylphenol (30 g, 0.22 mol) in methylene chloride (400 ml), sodium hydroxide (18.8 g, 0.44 mol) in water (400 ml), 1,3-dibromopropane (100 g, 1 mol) and tetra-n-butylammonium bisulfate (80 g, 0.22 mol). Distillation of the crude product yielded 55 g (75%) of pure material, b.p. 85°-87° (0.1 mm Hg).

Workup

  1. distillationDistillation of the crude product

Sources & evidence

ORD record
ord-2a306cf7138a4bbf9195735e82c70182
Source dataset
uspto-grants-1989_02
Patent number
US04808729

Reaction notes

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