Hydrochloric Acid → 4-Methylcatechol

HRID 1156445Notes

Reaction equation

HRID 1156445 reaction equation
[OH-:1].[Na+].OO.[CH2:5]([C:9](C)=[O:10])C(C)C.Cl.N1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:14][C:15]1[CH:5]=[C:9]([OH:10])[C:18](=[CH:17][CH:16]=1)[OH:1]

Participants

8

Procedure

Then, 0.9 mol of 30% sodium hydroxide was added to a mixture solution composed of 0.8 mol of the thus-obtained compound (III-1), 0.9 mol of 30% hydrogen peroxide, 0.008 mol of tetra-n-butylammonium bromide, a 2-fold amount by weight of methyl isobutyl ketone, a 2.7-fold amount by weight of water, and a 0.2-fold amount by weight of pyridine, the respective amounts being based on the weight of (III-1), at 0° to 10° C. over 3 hours. Stirring was continued for 3 hours at the same temperature. After completion of the reaction, the reaction mixture was rendered weakly acidic with hydrochloric acid, followed by extracting with methyl isobutyl ketone. After liquid separation, the methyl isobutyl ketone was distilled off from the organic layer to obtain 4-methylcatechol (V) in 93% yield.

Workup

  1. customAfter completion of the reaction
  2. extractionby extracting with methyl isobutyl ketone
  3. customAfter liquid separation
  4. distillationthe methyl isobutyl ketone was distilled off from the organic layer

Sources & evidence

ORD record
ord-c6c791acdc0b4c43b55e133475d6e784
Source dataset
uspto-grants-1982_06
Patent number
US04335263

Reaction notes

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