O-Cresol → HCID 11198199, compound

HRID 992767Notes

Reaction equation

HRID 992767 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:11][O:12]/[N:13]=[C:14](\[C:19]1[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:26]Br)/[C:15]([O:17][CH3:18])=[O:16].O>CN(C=O)C>[CH3:11][O:12]/[N:13]=[C:14](\[C:19]1[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:26][O:7][C:6]1[CH:5]=[CH:4][CH:3]=[CH:2][C:1]=1[CH3:8])/[C:15]([O:17][CH3:18])=[O:16]

Participants

6

Reactant 4

HCID 335O-CresolHCID 962WaterHCID 24758Sodium hydrideHCID 10957539HCID 10957539, compound

Product 1

HCID 11198199HCID 11198199, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

o-Cresol (5.9 g, 0.542 mol) was added to a suspension solution of sodium hydride (95%, 2 g, 0.813 mol) in DMF (100 mL) at 0 ° C., the reaction mixture was stirred for 1 hour at room temperature. This above reaction solution was added dropwise to a solution of methyl E-2-bromomethyl-6-methylphenylglyoxylate O-methyl oxime (16.2 g, 0.542 mol) in DMF (100 mL) for 30 min at 0 ° C. After was stirred for 1 hour at room temperature, the reaction mixture was added water (200 mL) and extracted with ether (100 mL) three times. The combined organic layers were washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the crude product which was used in the next reaction without further purification.

Workup

  1. stirringAfter was stirred for 1 hour at room temperature
  2. extractionextracted with ether (100 mL) three times
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56ec1ed0170c4ac3b76dbae2c3d8a26b
Source dataset
uspto-grants-2002_10
Patent number
US06469209B1

Reaction notes

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