Chloromethyl Methyl Ether → HCID 21531477, compound

HRID 1657925Notes

Reaction equation

HRID 1657925 reaction equation
[Br:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[CH:6][C:5]([CH:11]([CH3:13])[CH3:12])=[C:4]([Br:14])[C:3]=1[OH:15].CO[CH2:18][Cl:19]>C(=S)=S>[Br:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([CH2:18][Cl:19])[C:5]([CH:11]([CH3:13])[CH3:12])=[C:4]([Br:14])[C:3]=1[OH:15]

Participants

4

Reactant 2

HCID 7864Chloromethyl Methyl EtherHCID 21531652HCID 21531652, compound

Product 1

HCID 21531477HCID 21531477, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

Three hundred thirty-six parts of 2,6-dibromo-3,5-diisopropylphenol [prepared as described in Canad, J. Chem., Vol. 41, p. 1653 (1963)] is allowed to react with 130 parts of chloromethyl methyl ether and 80 parts of stannic chloride in 400 parts of carbon disulfide under general conditions set forth in "Organic Reactions", Vol. 1, p. 68 and 69. The reaction mixture is poured on ice, and the organic layer is separated and dried over anhydrous calcium sulfate. The solvent is allowed to evaporate and the residue is crystallized to give a pure sample of the title compound. Chloromethylation of the following monohalo- or dihalodialkylphenols gives the corresponding chloromethyl derivatives.

Workup

  1. additionThe reaction mixture is poured on ice
  2. customthe organic layer is separated
  3. dry with materialdried over anhydrous calcium sulfate
  4. customto evaporate
  5. customthe residue is crystallized

Sources & evidence

ORD record
ord-084eecd05995446e97673145b55588db
Source dataset
uspto-grants-1976_06
Patent number
US03962307

Reaction notes

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