Hydrogen Peroxide → (1-Chloro-1-methylethyl)benzene

HRID 1389270Notes

Reaction equation

HRID 1389270 reaction equation
OO.C1(O)C=CC=CC=1.O.CC(C1C=CC=CC=1)=C.[C:20]([Cl:29])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:22])[CH3:21]>CC(C1C=CC=CC=1)=C>[C:20]([Cl:29])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 784Hydrogen Peroxide4×HCID 962Water2×HCID 996Phenol3×HCID 20298920HCID 20298920, compound

Product 1

HCID 70281(1-Chloro-1-methylethyl)benzene

Reagents, catalysts & solvents 1

HCID 7407Alpha-MethylstyreneSolvent2×

Procedure

A solution of 110.5 grams of cumyl chloride in 854.8 grams of α-methylstyrene was prepared and charged to a 1000 ml reservoir. A solution of 200 grams of 70% hydrogen peroxide was charged to a 500 ml reservoir and 175 grams of liquified phenol (90%) was charged to a 250 ml reservoir. All the reservoirs were individually connected to metering pumps. To the first reactor was added 197.3 grams of α-methylstyrene and 36.8 grams of liquified phenol. The temperature in R1 was adjusted to 27° C. by circulating warm water through the jacket. To this solution was added 25.5 grams of t-cumyl chloride and then 36.8 grams of 70% hydrogen peroxide were added dropwise from a dropping funnel over 15 minutes. The temperature in R1 was allowed to rise to 35° C.±1° C. during this period. The temperature was controlled at 35° C. throughout the remainder of the run by circulating 30° C. water through the reactor jacket. At the end of the hydrogen peroxide addition the metering pumps and varistaltic pumps were activated. The α-methylstyrene-cumyl chloride solution was pumped into R1 at a rate of 5.094 grams/minute. The 70% hydrogen peroxide solution as pumped into R1 at a rate of 0.839 grams/minute and the liquified phenol was pumped in at a rate of 0.804 grams/minute.

Workup

  1. additioncharged to a 1000 ml reservoir
  2. additionwas charged to a 250 ml reservoir
  3. customwas adjusted to 27° C.
  4. waitto rise to 35° C.±1° C. during this period
  5. customwas controlled at 35° C. throughout the remainder of the run
  6. customby circulating 30° C.

Sources & evidence

ORD record
ord-34e62ccc8910430aab79d2fde40375f8
Source dataset
uspto-grants-1981_01
Patent number
US04243821

Reaction notes

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