Chloromethyl Methyl Ether → HCID 22099451, compound

HRID 1457593Notes

Reaction equation

HRID 1457593 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]=[N:12][C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:14]=2[OH:25])=[CH:7][CH:6]=1.[CH3:26][O:27][CH2:28]Cl.[Cl-].[NH4+]>O1CCCC1.CN(C)C=O>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]=[N:12][C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([C:21]([CH3:22])([CH3:24])[CH3:23])[C:14]=2[O:25][CH2:26][O:27][CH3:28])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 135719544195314-31-9

Product 1

HCID 22099451HCID 22099451, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 63 g of 62.5% sodium hydride and 2500 ml of dimethylformamide (DMF) was added dropwise under ice-cooling 3000 ml of a tetrahydrofuran (THF) solution containing 472 g of 2-(4-methoxyphenylazo)-4-methoxy-6-tert-butylphenol. After elevating the temperature to room temperature, the mixture was ice-cooled again, and 133 g of methoxymethyl chloride was added dropwise. After stirring at room temperature for 2 hours, 300 ml of an aqueous saturated ammonium chloride solution was gradually added dropwise to the mixture. THF was removed under reduced pressure, and a saturated saline solution was added to the residue. The mixture was extracted with ethyl acetate. The extract was washed and dried, and the solvent was removed under reduced pressure. The precipitated crystals were recrystallized from a mixed solution of hexane and ethyl acetate to give 520 g of [2-(4-methoxyphenylazo)-4-methoxy-6-tert-butylphenoxy]methoxymethane (yield: 97%, melting point: 102°-103° C., IR: 1610 cm-1).

Workup

  1. additionwas added dropwise under ice-
  2. customto room temperature
  3. temperaturecooled again
  4. customTHF was removed under reduced pressure
  5. additiona saturated saline solution was added to the residue
  6. extractionThe mixture was extracted with ethyl acetate
  7. washThe extract was washed
  8. customdried
  9. customthe solvent was removed under reduced pressure
  10. customThe precipitated crystals were recrystallized from a mixed solution of hexane and ethyl acetate

Sources & evidence

ORD record
ord-40b12ee244924acfadab7799cc0150cb
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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