Water → 1-(Methoxymethoxy)-4-methylbenzene

HRID 1492545Notes

Reaction equation

HRID 1492545 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.C(N(C(C)C)CC)(C)C.[CH3:18][O:19][CH2:20]Cl.O>C(Cl)Cl>[CH3:18][O:19][CH2:20][O:7][C:6]1[CH:5]=[CH:4][C:3]([CH3:8])=[CH:2][CH:1]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2879P-CresolHCID 7864Chloromethyl Methyl EtherHCID 81531Diisopropylethylamine

Product 1

HCID 113441131-(Methoxymethoxy)-4-methylbenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Cresol (59 g) was dissolved in 500 ml of methylene chloride, followed by addition of 238 ml of diisopropylethylamine and 66 g of chloromethyl methyl ether, and stirred at room temperature for two nights. The reaction solution was poured into water, which was then extracted with methylene chloride. After washing in 2N hydrogen chloride and then washing in saturated aqueous sodium chloride, the extract was dried over anhydrous sodium sulfate to yield residue. The residue was subjected to chromatography which was eluted with chloroform, to obtain 4-tolyl methoxymethyl ether.

Workup

  1. extractionwas then extracted with methylene chloride
  2. washAfter washing in 2N hydrogen chloride
  3. washwashing in saturated aqueous sodium chloride
  4. dry with materialthe extract was dried over anhydrous sodium sulfate
  5. customto yield residue
  6. washwas eluted with chloroform

Sources & evidence

ORD record
ord-35b3654269cc4508980188f68ad5e7f7
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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