Hydrogen Bromide → HCID 20200706, compound

HRID 979632Notes

Reaction equation

HRID 979632 reaction equation
[C:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:12][CH:13]=[CH2:14])(=[O:3])[CH3:2].[BrH:15].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>CCCCCC>[C:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:12][CH2:13][CH2:14][Br:15])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 7187Benzoyl PeroxideHCID 57268533Phenol, 2-methyl-6-(2-propen-1-yl)-, 1-acetate

Product 1

HCID 20200706HCID 20200706, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

The protected monohydroxy compound, 1-acetoxy,2-(2 propenyl)-6-methylbenzene was the starting material. Halogenation was achieved by bubbling HBr through a hexane solution (250 ml.) of the starting material (61.3 g, 0.323 moles) and dibenzoyl peroxide (2 g) for 2 hours. The reaction mixture was washed twice with saturated NaHCO3 solution (2×200 ml.) and once with H2O. The hexane layer was dried over Na2SO4 and the solvent evaporated. The desired 1-acetoxy,2-(3-bromopropyl)-6-methylbenzene was isolated by distillation. The % yield was 58.1% (40.84 g, BP=164°-166° C. at 0.03 Torr).

Workup

  1. washThe reaction mixture was washed twice with saturated NaHCO3 solution (2×200 ml.) and once with H2O
  2. dry with materialThe hexane layer was dried over Na2SO4
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-076d2668e4ba47dca1afd4072cf93799
Source dataset
uspto-grants-1987_05
Patent number
US04668739

Reaction notes

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