1,5-Dihydroxynaphthalene → 1,5-Bis(octyloxy)naphthalene

HRID 525981

反応式

HRID 525981 の反応式
O[C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[C:22](=[O:25])([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:14]([O:12][C:7]1[C:6]2[C:11](=[C:2]([O:25][CH2:22][CH2:10][CH2:11][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:3]=[CH:4][CH:5]=2)[CH:10]=[CH:9][CH:8]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

参加物

5

反応物 3

HCID 67491,5-DihydroxynaphthaleneHCID 81401-BromooctaneHCID 11430Potassium Carbonate

生成物 1

HCID 509011751,5-Bis(octyloxy)naphthalene収率 140.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

1,5-dihydroxynaphthalene (2.95 g, 18.4 mmol), 1-bromooctane (8.2 g, 42.5 mmol), and potassium carbonate (50 g, 0.36 mol) was mixed in N,N-dimethylformamide and heated at 90° C. for 5 h. The potassium carbonate was filtered off and the reaction mixture was quenched with water and extracted two times with ether. The combined organic phase was then washed once with 1M HCl, two times with water, and evaporated. The residual brown solid was recrystallised in ethanol to form 1,5-bis(octyloxy)naphthalene (4.96 g, 12.9 mmol) as brown crystals. 1H-NMR (CDCl3, δ): 0.89 (t, 6H), 1.2-1.4 (m, 16H), 1.4-1.6 (m, 4H), 1.91 (m, 4H), 4.12 (t, 4H), 6.81 (d, 2H), 7.34 (t, 2H), 7.83 (d, 2H) MS MALDI-TOF (m/z): 384.266

後処理

  1. filtrationThe potassium carbonate was filtered off
  2. customthe reaction mixture was quenched with water
  3. extractionextracted two times with ether
  4. washThe combined organic phase was then washed once with 1M HCl, two times with water
  5. customevaporated
  6. customThe residual brown solid was recrystallised in ethanol

出典と根拠

ORDレコード
ord-9909275f86894bd9a2aaf61545134d1e
出典データセット
uspto-grants-2016_05
特許番号
US09343198B2

関連ノート

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