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

HRID 1645404노트

반응식

HRID 1645404 반응식
[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

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 4055Menadione

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e7745c70daf94e29a47547374cda35e6
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124793B2

반응 노트

불러오는 중…