Hydrogen Peroxide → 2-(3-Hydroxypropyl)-6-methylphenol

HRID 258341Notes

Reaction equation

HRID 258341 reaction equation
B.[OH2:2].[OH-].[Na+].OO.[CH2:7]([C:10]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:11]=1[O:12][Si](C)(C)C)[CH:8]=[CH2:9]>O1CCCC1>[OH:2][CH2:9][CH2:8][CH2:7][C:10]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:11]=1[OH:12]

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 962WaterHCID 6331BoraneHCID 14798Sodium HydroxideHCID 197375892-Allyl-6-methylphenoxytrimethylsilane

Product 1

HCID 543527972-(3-Hydroxypropyl)-6-methylphenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In dry tetrahydrofuran (abbreviated as THF) was dissolved 42.7 parts of the above-obtained 2-allyl-6 -methylphenoxytrimethylsilane in a nitrogen atmosphere. Thereto was added dropwise at 5° C. 86.2 parts of a 1 mol/l THF solution of a borane, and this mixture was allowed to react at 20° C. for 1 hour. To the resulting reaction mixture was added 15 parts of pure water, followed by 45 parts of 10% aqueous sodium hydroxide solution. Subsequently, 40 parts of 30% hydrogen peroxide was added dropwise to the reaction mixture at 40° C. and reaction was further conducted at 50° C. for 1 hour. Through extraction with diethyl ether, the desired compound, 2-(3 hydroxypropyl)-6-methylphenol, was obtained from the reaction mixture.

Workup

  1. additionThereto was added dropwise at 5° C
  2. customto react at 20° C. for 1 hour
  3. customTo the resulting reaction mixture
  4. customreaction
  5. extractionThrough extraction with diethyl ether

Sources & evidence

ORD record
ord-55d7cb2d8d884b3796680ff0688964a6
Source dataset
uspto-grants-1993_11
Patent number
US05266673

Reaction notes

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