Hydrochloric Acid → 5-(Chloromethyl)-6-methylbenzo[d][1,3]dioxole

HRID 1841374Notes

Reaction equation

HRID 1841374 reaction equation
Cl.C[CH:3]1[O:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[O:4]1.[CH2:12]=O.[CH2:14]([Cl:16])Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:16][CH2:14][C:9]1[C:10]([CH3:12])=[CH:11][C:5]2[O:4][CH2:3][O:7][C:6]=2[CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 6344DichloromethaneHCID 841672-Methyl-2H-1,3-benzodioxole

Product 1

HCID 105594165-(Chloromethyl)-6-methylbenzo[d][1,3]dioxole

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

To a mixture of methylene chloride (130 L), concentrated HCl (130 L), and tetrabutylammonium bromide (1.61 Kg) was added 5 methylbenzo[d][1,3]dioxole (10 Kg) followed by the slow addition of formaldehyde (14 L, 37 wt % in water). The mixture was stirred overnight. The organic layer was separated, dried with magnesium sulfate and concentrated to an oil. Hexane (180 L) was added and the mixture heated to boiling. The hot hexane solution was decanted from a heavy oily residue and evaporated to give almost pure 5-chloromethyl-6-methylbenzo[d][1,3]dioxole as a white solid. Recrystallization from hexane (50 L) gave 5-chloromethyl-6-methylbenzo[d][1,3]dioxole (80% recovery after recrystallization).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried with magnesium sulfate
  3. concentrationconcentrated to an oil
  4. additionHexane (180 L) was added
  5. temperaturethe mixture heated to boiling
  6. customThe hot hexane solution was decanted from a heavy oily residue
  7. customevaporated

Sources & evidence

ORD record
ord-a8539749e57045f48562d99a5d4e6f99
Source dataset
uspto-grants-2004_01
Patent number
US06683103B2

Reaction notes

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