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

HRID 990036Notes

Reaction equation

HRID 990036 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:11]=[CH:10][C:6]2[O:7][CH2:8][O:9][C:5]=2[CH:4]=1.[CH2:12]=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[Cl:1][CH2:2][C:3]1[C:11]([CH3:12])=[CH:10][C:6]2[O:7][CH2:8][O:9][C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 815641,3-Benzodioxole, 5-methyl-

Product 1

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

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

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-9705cc443b4a4d56b8f950dc11c6f367
Source dataset
uspto-grants-2002_10
Patent number
US06458805B2

Reaction notes

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