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Ethylene Glycol → 3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]cyclohex-3-en-1-one ethylene ketal

HRID 1762248
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HRID 1762248 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:10]=1[C:24]1[CH2:29][CH2:28][CH2:27][C:26](=[O:30])[CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:31](O)[CH2:32][OH:33].C1(C=CC(O)=CC=1)O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:32]1[O:33][C:26]2([CH2:27][CH2:28][CH:29]=[C:24]([C:10]3[CH:11]=[CH:12][C:13]([C:15]([CH3:22])([CH3:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:14][C:9]=3[O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:25]2)[O:30][CH2:31]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 174Ethylene GlycolHCID 785HydroquinoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 198553803-[2-Benzyloxy-4-(1,1-Dimethylheptyl)phenyl]cyclohex-2-enone

생성물 1

HCID 572072353-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]cyclohex-3-en-1-one ethylene ketal

시약·촉매·용매 1

HCID 241
Benzene
용매

실험 절차

A solution of 500 mg. of 3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]cyclohex-2-en-1-one, 7.8 g. of ethylene glycol, 375 mg. of hydroquinone and 50 mg. of p-toluenesulfonic acid monohydrate in 50 ml. of benzene is heated at reflux for 12 hours using a DeanStark condensor filled with 3A molecular sieves. The reaction is cooled, added to 500 ml. saturated sodium bicarbonate and the quenched mixture extracted with three 150 ml. portions of ether, dried over magnesium sulfate and evaporated to a solid. This solid is purified via column chromatography on 50 g. of silica gel eluted with 50% ether-petroleum ether to yield the title product.

후처리

  1. temperatureat reflux for 12 hours
  2. temperatureThe reaction is cooled
  3. additionadded to 500 ml
  4. extractionsaturated sodium bicarbonate and the quenched mixture extracted with three 150 ml
  5. dry with materialportions of ether, dried over magnesium sulfate
  6. customevaporated to a solid
  7. customThis solid is purified via column chromatography on 50 g
  8. washof silica gel eluted with 50% ether-petroleum ether

출처 및 근거

ORD 기록
ord-02b3d3a5f4c747d380a3ee42e1e24e2d
출처 데이터셋
uspto-grants-1989_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04831059

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