Chloromethyl Methyl Ether → HCID 21531695, compound

HRID 1657926Notes

Reaction equation

HRID 1657926 reaction equation
[Br:1][C:2]1[C:3]([CH:13]([CH3:15])[CH3:14])=[C:4]([CH:6]=[C:7]([CH:10]([CH3:12])[CH3:11])[C:8]=1[OH:9])[OH:5].[Cl:16][CH2:17]OC>C(=S)=S>[Br:1][C:2]1[C:8]([OH:9])=[C:7]([CH:10]([CH3:11])[CH3:12])[C:6]([CH2:17][Cl:16])=[C:4]([C:3]=1[CH:13]([CH3:15])[CH3:14])[OH:5]

Participants

4

Reactant 2

HCID 7864Chloromethyl Methyl EtherHCID 21531975HCID 21531975, compound

Product 1

HCID 21531695HCID 21531695, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

Two hundred seventy-three parts of 3-bromo-2,5-diisopropylhydroquinone is allowed to react with 130 parts of chloromethylmethyl 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 dihalodialkylhydroquinones or resorcinols 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-d791c1ff5ef6413084f07e769df1b00c
Source dataset
uspto-grants-1976_06
Patent number
US03962307

Reaction notes

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