Chloromethyl Methyl Ether → 3-Chloro-4-methoxymethoxy-5-methyl-1-benzoyloxybenzene

HRID 363108Notes

Reaction equation

HRID 363108 reaction equation
[C:1]([O:9][C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([OH:17])=[C:12]([Cl:18])[CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][CH2:21]Cl.C(N(C(C)C)C(C)C)C>C(Cl)(Cl)Cl>[Cl:18][C:12]1[CH:11]=[C:10]([O:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:15]=[C:14]([CH3:16])[C:13]=1[O:17][CH2:19][O:20][CH3:21]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 185045884-Benzoyloxy-2-chloro-6-methylphenol

Product 1

HCID 185046333-Chloro-4-methoxymethoxy-5-methyl-1-benzoyloxybenzeneYield 96%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

Then, 25 g of 4-benzoyloxy-2-chloro-6-methylphenol was dissolved in 250 ml of chloroform, to which 12 g of chloromethyl methyl ether was added, while stirring at 0° C., and 21 g of N-ethyldiisopropylamine was added dropwise. After heating under reflux for 1 hour, the chloroform layer was washed with water, and concentrated. The residue was subjected to silica gel chromatography, which afforded 27.4 g of 3-chloro4-methoxymethoxy-5-methyl-1-benzoyloxybenzene (96% yield).

Workup

  1. additionwas added
  2. temperatureAfter heating
  3. temperatureunder reflux for 1 hour
  4. washthe chloroform layer was washed with water
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a574c8b2193b414c9c87ec3f2a6ac32f
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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