2,6-Bis(4-methoxymethyloxy-3-methoxybenzylidene)cyclohexanone → Cyclovalone

HRID 77678노트

반응식

HRID 77678 반응식
COC[O:4][C:5]1[CH:31]=[CH:30][C:8]([CH:9]=[C:10]2[CH2:15][CH2:14][CH2:13][C:12](=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([O:23]COC)=[C:19]([O:27][CH3:28])[CH:18]=3)[C:11]2=[O:29])=[CH:7][C:6]=1[O:32][CH3:33]>CO.Cl>[OH:23][C:20]1[CH:21]=[CH:22][C:17]([CH:16]=[C:12]2[CH2:13][CH2:14][CH2:15][C:10](=[CH:9][C:8]3[CH:30]=[CH:31][C:5]([OH:4])=[C:6]([O:32][CH3:33])[CH:7]=3)[C:11]2=[O:29])=[CH:18][C:19]=1[O:27][CH3:28]

참가 물질

4

반응물 1

HCID 695017962,6-Bis(4-methoxymethyloxy-3-methoxybenzylidene)cyclohexanone

생성물 1

HCID 11366Cyclovalone수율 66%

시약·촉매·용매 2

HCID 313Hydrochloric Acid촉매HCID 887Methanol용매

실험 절차

2,6-Bis(4-methoxymethyloxy-3-methoxybenzylidene)cyclohexanone (38j, 0.49 g, 1.1 mmol) was dissolved in methanol (100 ml) and stirred for 15 min at room temperature. Concentrated hydrochloric acid (3 drops) was added and the mixture stirred for 3 hr at 60° C. The methanol was evaporated and the resulting residue extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was recrystallized from ethanol to give 0.26 g (66%) of a yellow solid: mp 177-178° C. [expected mp 179-181° C.]; 1H NMR: δ 1.79 (m, 2H), 2.90 (t, 4H, J=5.4 Hz), 3.89 (s, 6H), 5.88 (s, 2H), 6.91 (s, 2H), 6.96 (d, 2H, J=4.8 Hz), 7.06 (d, 2H, J=8.0 Hz), 7.72 (s, 2H); 13C NMR: δ 23.1, 28.5, 56.0, 113.2, 114.4, 124.4, 128.5, 134.2, 136.9, 146.2, 146.4, 172.8.

후처리

  1. stirringthe mixture stirred for 3 hr at 60° C
  2. customThe methanol was evaporated
  3. extractionthe resulting residue extracted into ethyl acetate
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto afford a solid
  9. customThe crude solid was recrystallized from ethanol

출처 및 근거

ORD 기록
ord-06c31b1e0be04546bf5a41e0ee01f7e8
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841326B2

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