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Ethylene Glycol → Trans-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(2-propenyl)cyclohexanone ethylene ketal

HRID 1650046
ノート
印刷プレビュー

反応式

HRID 1650046 の反応式
[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@H:24]1[C@H:29]([CH2:30][CH:31]=[CH2:32])[CH2:28][CH2:27][C:26](=[O:33])[CH2:25]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:34](O)[CH2:35][OH:36].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>CCCCC.CCOCC.C1C=CC=CC=1>[CH2:35]1[O:36][C:26]2([CH2:27][CH2:28][C@@H:29]([CH2:30][CH:31]=[CH2:32])[C@H: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:33][CH2:34]1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 174Ethylene GlycolHCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 13105165Trans-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(2-propenyl)cyclohexanone

生成物 1

HCID 86738780Trans-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(2-propenyl)cyclohexanone ethylene ketal

試薬・触媒・溶媒 3

HCID 241
Benzene
溶媒
HCID 3283Diethyl Ether溶媒
HCID 8003Pentane溶媒

実験手順

A mixture of 17.0 g. (38.1 mmoles) of trans-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(2-propenyl)cyclohexanone, 47.2 g. (0.762 mole) ethylene glycol and 250 mg. of p-toluenesulfonic acid monohydrate in 200 ml. of benzene was heated at reflux for 3 hours with a Dean-Stark trap. The reaction was cooled and added to 200 ml. 1N sodium hydroxide, 100 ml. ether and 100 ml. pentane. The organic extract was washed twice with 200 ml. portions of water, twice with 200 ml. portions of saturated sodium chloride, dried over magnesium sulfate and evaporated (aspirator) giving a quantitative yield of the title compound.

後処理

  1. additionA mixture of 17.0 g
  2. temperatureat reflux for 3 hours with a Dean-Stark trap
  3. temperatureThe reaction was cooled
  4. additionadded to 200 ml
  5. extractionThe organic extract
  6. washwas washed twice with 200 ml
  7. dry with materialportions of saturated sodium chloride, dried over magnesium sulfate
  8. customevaporated (aspirator)

出典と根拠

ORDレコード
ord-fbeae92f5a764751927c9b3060684f9d
出典データセット
uspto-grants-1990_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04921994

反応ノート

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