Hydrogen Peroxide → HCID 22982059, compound

HRID 1473742Notes

Reaction equation

HRID 1473742 reaction equation
[C:1]([O:6][C:7]1[CH:12]=[CH:11][C:10](Cl)=[CH:9][CH:8]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2].[Mg].B(OC)(OC)[O:16]C.OO>C(O)(=O)C.O1CCCC1>[CH3:5][CH2:4][C:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:16])=[CH:9][CH:8]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 8470Trimethyl borateHCID 3021210HCID 3021210, compoundHCID 5462224Magnesium

Product 1

HCID 22982059HCID 22982059, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

A Grignard reagent was previously prepared using 99.3 g of 1-tert-amyloxy-4-chlorobenzene, 12.76 g of magnesium, and 200 mL of tetrahydrofuran. To the Grignard reagent, 57.1 g of trimethyl borate was added dropwise at an internal temperature below −50° C. At a reaction temperature of 5° C., stirring was continued for 3 hours. Thereafter, at an internal temperature below 30° C., 45.0 g of acetic acid and 145.7 g of 35% hydrogen peroxide solution were added. At room temperature, stirring was continued for 3 hours. Standard work-up and purification by silica gel chromatography gave 62.2 g of 4-tert-amyloxy-1-phenol (yield 69%).

Workup

  1. stirringAt room temperature, stirring
  2. waitwas continued for 3 hours
  3. customStandard work-up and purification by silica gel chromatography

Sources & evidence

ORD record
ord-d919bfed7dc04e7fa2ace3de1c2659db
Source dataset
uspto-grants-2015_04
Patent number
US09017918B2

Reaction notes

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