Water → HCID 89825893, compound

HRID 625700Notes

Reaction equation

HRID 625700 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.[OH:11][C:12]([CH3:27])([CH3:26])[CH2:13][CH2:14]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH2:14][CH2:13][C:12]([CH3:27])([OH:11])[CH3:26])=[C:4]([CH3:10])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 169194-Bromo-2,6-dimethylphenolHCID 140012952-Methyl-4-[(4-methylbenzenesulfonyl)oxy]butan-2-ol2×

Product 1

HCID 89825893HCID 89825893, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-Bromo-2,6-dimethylphenol (2.00 g, 9.95 mmol), toluene-4-sulfonic acid 3-hydroxy-3-methyl-butyl ester (Intermediate 10, 2.83 g, 10.9 mmol) and potassium carbonate (1.01 g, 10.9 mmol) are combined in N,N-dimethylformamide (50 mL) and heated at 80° C. for 24 hours. The mixture is cooled, poured into water and extracted with diethyl ether. The organic phase is dried and the solvent removed. The residue is purified by flash chromatography (0-50% ethyl acetate in cyclohexane) to give the title compound (Yield 2.00 g). GC (METHOD 1): tR=11.26 min; Mass spectrum (EI+): m/z=286/288 [M]+.

Workup

  1. temperatureThe mixture is cooled
  2. extractionextracted with diethyl ether
  3. customThe organic phase is dried
  4. customthe solvent removed
  5. customThe residue is purified by flash chromatography (0-50% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-b82e9098c83c48a38056fe2c6e34e2c8
Source dataset
uspto-grants-2016_04
Patent number
US09308194B2

Reaction notes

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