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

HRID 525981

반응식

HRID 525981 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 509011751,5-Bis(octyloxy)naphthalene수율 140.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-9909275f86894bd9a2aaf61545134d1e
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09343198B2

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