m-Chloroperbenzoic acid → HCID 20530805, compound

HRID 1730371Notes

Reaction equation

HRID 1730371 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([C:15]1[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:18]([OH:25])=[C:17]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:16]=1)[CH:13]=[CH2:14]>C(Cl)Cl>[C:21]([C:19]1[CH:20]=[C:15]([CH:16]=[C:17]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:18]=1[OH:25])[CH2:12][CH:13]1[CH2:14][O:9]1)([CH3:22])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 109228432,6-Di-tert-butyl-4-(prop-2-en-1-yl)phenol

Product 1

HCID 20530805HCID 20530805, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 22.4 g [0.11 mol] of m-chloroperbenzoic acid [85% strength] in 300 ml of dry methylene chloride is added dropwise to a solution of 24.6 g [0.10 mol] of 4-allyl-2,6-di-tert.-butylphenol of boiling point6 : 134°-36° C [manufactured according to the datain Journ. Org. Chem. USSR 1967, 95] in 175 ml of dry methylene chloride at room temperature, at a speed such that the temperature of the reaction solution does not exceed room temperature. Stirring is continued at room temperature until a sample of the reaction solution indicates that 1 equivalent of peracid has been consumed. Thereafter, excess peracid is destroyed by adding 10% strength aqueous sodium sulphate solution and the organic phase is successively extracted with 5% strength sodium bicarbonate solution and with water, dried over sodium sulphate and evaporated. Crude 3,5-di-tert.-butyl-4-hydroxybenzyl-oxirane is obtained as a brownish oil which, when recrystallized from petroleum ether, yields colorless crystals of melting point 86°-87° C.

Workup

  1. custom134°-36° C
  2. customat room temperature
  3. customdoes not exceed room temperature
  4. customis continued at room temperature until a sample of the reaction solution
  5. customhas been consumed
  6. customThereafter, excess peracid is destroyed
  7. additionby adding 10% strength aqueous sodium sulphate solution
  8. extractionthe organic phase is successively extracted with 5% strength sodium bicarbonate solution and with water
  9. dry with materialdried over sodium sulphate
  10. customevaporated

Sources & evidence

ORD record
ord-caaf874d6461403eb1385ae4a2b0ddf2
Source dataset
uspto-grants-1976_11
Patent number
US03992420

Reaction notes

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