Hydrochloric Acid → 2-(Chloromethyl)-3-methylnaphthalene-1,4-dione

HRID 1645404Notes

Reaction equation

HRID 1645404 reaction equation
[CH3:1][C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=O)[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH2:14]=[O:15].[ClH:16]>C(O)(=O)C>[CH3:1][C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:14](=[O:15])[C:11]=1[CH2:10][Cl:16])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 4055Menadione

Product 1

HCID 1234392-(Chloromethyl)-3-methylnaphthalene-1,4-dioneYield 55%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 17.2 g (0.1 mole) of 2-methyl-1,4-napthoquinone and 6 g (0.2 mole) of paraformaldehyde was heated to 60° C. in 50 mL of glacial acetic acid and stirred while dry HCl was bubbled through the solution for about 3 hrs. To the cooled mixture was added 200 mL of water, the solid was filtered and rinsed with 50 mL of water. It was then suspended in 200 mL of CH2Cl2, filtered, rinsed with CH2Cl2, and the filtrate was water washed, dried, and evaporated to leave 20.5 g of crude 2-methyl-3-chloromethyl-1,4-napthoquinone. The crude product was purified by sublimation at about 100° C. and pressure of 0.05 mm to give 12.7 g. Since there had been some splatter during the sublimation, the product was resublimed to give 12.1 g (55% yield), m.p. 102-104° C.

Workup

  1. customwas bubbled through the solution for about 3 hrs
  2. additionTo the cooled mixture was added 200 mL of water
  3. filtrationthe solid was filtered
  4. washrinsed with 50 mL of water
  5. filtrationfiltered
  6. washrinsed with CH2Cl2
  7. washwashed
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-e7745c70daf94e29a47547374cda35e6
Source dataset
uspto-grants-2012_02
Patent number
US08124793B2

Reaction notes

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