Hydrochloric Acid → Benzene, (1,1-dimethylethoxy)-

HRID 1389393Notes

Reaction equation

HRID 1389393 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1C(C(O[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=O)=CC=CC=1.Cl>CCOCC>[C:19]([O:18][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7961BromobenzeneHCID 11966tert-Butyl peroxybenzoateHCID 5462224Magnesium

Product 1

HCID 81179Benzene, (1,1-dimethylethoxy)-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In this example, phenyl t-butyl ether is prepared. Grignard reagent, phenyl magnesium bromide, is formed by mixing 100 g magnesium turnings with 607.7 g bromobenzene and 6170 g anhydrus ethyl ether. After formation of the Grignard reagent, t-butyl per benzoate (449 g) in ether is added at 15° C.-25° C. under nitrogen with stirring. Reaction product is shaken with cold, dilute hydrochloric acid, then washed with dilue aqueous sodium hydroxide, and then washed with water. It is then dried and distilled to yield 269.2 G of product phenyl t-butyl ether which is analyzed to give 79.1% C (calc 80.0%) and 9.2% H (calc 9.3%).

Workup

  1. customReaction product
  2. washwashed with dilue aqueous sodium hydroxide
  3. washwashed with water
  4. customIt is then dried
  5. distillationdistilled

Sources & evidence

ORD record
ord-f26e7df39ddf4606b19750286726010b
Source dataset
uspto-grants-1981_01
Patent number
US04244704

Reaction notes

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