Hydrochloric Acid → 1,4-Dimethoxyanthracene

HRID 2306904

反応式

HRID 2306904 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 831071,4-Dimethoxyanthracene収率 94%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
25 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-bc3c39ff19b445d39a69c2d89f9a6d4f
出典データセット
uspto-grants-2004_12
特許番号
US06828450B2

関連ノート

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