Hydrochloric Acid → 1,4-Dimethoxyanthracene

HRID 2306904

반응식

HRID 2306904 반응식
O[C:2]1[C:15]2[C:6](=[CH:7][C:8]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:5]([OH:16])=[CH:4][CH:3]=1.I[CH3:18].CN([CH:22]=[O:23])C.Cl>O>[CH3:18][O:16][C:5]1[C:6]2[C:15](=[CH:14][C:13]3[C:8]([CH:7]=2)=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:2]([O:23][CH3:22])=[CH:3][CH:4]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 12631814Anthracene-1,4-diol

생성물 1

HCID 831071,4-Dimethoxyanthracene수율 94%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
25 °C

실험 절차

To a 0.275 g (11.0 mmol) of pre-washed (with distilled diethyl ether) sodium hydride under argon were added 1.00 g (4.80 mmol) of 1,4-dihydroxyanthracene, 0.75 mL (12.0 mmol) of iodomethane, and 10 mL of DMF (distilled over CaH2). The solution was stirred at 25° C. for 1.5 h, diluted with 20 mL of water, and acidified with 6 N HCl (pH ˜2). The mixture was extracted three times with ethyl acetate, and the combined extract was washed twice with water, and brine, dried (MgSO4), concentrated to give 1.07 g (94% yield) of compound 2. Recrystallization from ether:hexane (1:1) gave 0.89 g (78% yield) of yellow solids: mp 132-133° C. (Lit.6 134-136° C.); MS, FAB, m/z 239 (M+1), 238 (M+); 1H NMR d 8.70 (s, 2H, C9,10H), 7,97 (dd, J=6.1, 3.6 Hz, 2H, C5,8H), 7.40 (dd, J=6.6, 3.2 Hz, 2H, C6,7H ), 6.55 (s, 2H, C2,3H), 3.97 (s, 6H, OCH3); 13C NMR d 149.5 (s, C8a,10a), 131.5 (s, C4a,9a), 128.5 (d, C9,10), 125.5 (d, C5,8), 120.7 (d, C6,7), 100.9 (d, C2,3), 55.6 (s, OCH3).

후처리

  1. washTo a 0.275 g (11.0 mmol) of pre-washed (with distilled diethyl ether) sodium hydride under argon
  2. extractionThe mixture was extracted three times with ethyl acetate
  3. extractionthe combined extract
  4. washwas washed twice with water, and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bc3c39ff19b445d39a69c2d89f9a6d4f
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06828450B2

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