Methanol → HCID 65364656, compound

HRID 1446426Notes

Reaction equation

HRID 1446426 reaction equation
[H-].[Na+].[CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])([CH3:5])[CH3:4].[CH3:13][O:14][CH2:15]Cl.CO>O1CCCC1.O>[CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][O:14][CH3:15])([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 887MethanolHCID 69432-IsopropylphenolHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydride

Product 1

HCID 65364656HCID 65364656, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Firstly, sodium hydride (275 mmol) was suspended in tetrahydrofuran (THF) (120 ml) and to this, 2-isopropylphenol (111 mmol, reference symbol A1 in FIG. 1) dissolved in THF (30 ml) was added dropwise at 0° C. After 30 minutes, chloromethyl methyl ether (221 mmol) was added to this solution and after heating to room temperature, the reaction was stopped by adding methanol and then water. The aqueous phase was extracted with ether. The organic phases were combined and washed with water and a saturated sodium chloride solution in that order and then dried using anhydrous sodium sulfate. After removing the drying agent by filtering, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography to obtain 1-isopropyl-2-methoxy methoxybenzene (17.5 g, 87% yield, reference symbol A2 in FIG. 1).

Workup

  1. additionwas added dropwise at 0° C
  2. extractionThe aqueous phase was extracted with ether
  3. washwashed with water
  4. dry with materiala saturated sodium chloride solution in that order and then dried
  5. customAfter removing the drying agent
  6. filtrationby filtering
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7a2f58571a27439fa20263b4a50cd066
Source dataset
uspto-grants-2010_02
Patent number
US07667078B2

Reaction notes

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