Sulfuric Acid → 4-(4-Chlorophenyl)-4-methyl-2-oxo-valeric acid

HRID 1444454ノート

反応式

HRID 1444454 の反応式
C([O:3][C:4](=[O:17])[CH:5](P(OCC)(OCC)=O)[O:6]CC)C.C([N-]C(C)C)(C)C.[Li+].[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([CH3:37])([CH3:36])[CH:34]=O)=[CH:29][CH:28]=1.S(=O)(=O)(O)O>O1CCCC1.O1CCCC1.CCCCCCC.C1(C)C=CC=CC=1>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([CH3:37])([CH3:36])[CH2:34][C:5](=[O:6])[C:4]([OH:3])=[O:17])=[CH:29][CH:28]=1

参加物

7

反応物 4

HCID 1118Sulfuric AcidHCID 314825Ethyl 2-diethoxyphosphoryl-2-ethoxyacetateHCID 2724682Lithium diisopropylamideHCID 114353342-(4-Chlorophenyl)-2-methylpropanal

生成物 1

HCID 219488514-(4-Chlorophenyl)-4-methyl-2-oxo-valeric acid収率 81.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 22168748HCID 22168748、化合物溶媒

反応条件

温度
0 °C

実験手順

A solution of 15.04 g of 2-diethylphosphono-2-ethoxyacetic acid-ethyl ester in 50 ml of tetrahydrofuran is mixed with 30 ml of a 2 M solution of lithium diisopropylamide in tetrahydrofuran-heptane-toluene while being cooled with ice within 20 minutes, and it is stirred for 15 minutes at 0° C. Within 30 minutes, a solution of 10.2 g of 2-(4-chlorophenyl)-2-methylpropanal in 50 ml of tetrahydrofuran is added thereto at 0° C. After 20 hours at room temperature, 2N sulfuric acid is added, it is extracted with ethyl acetate, dried (Na2SO4) and concentrated by evaporation. The crude product is saponified with 200 ml of 2 M sodium hydroxide solution/400 ml of ethanol. 13.8 g of acid, which is refluxed for 3 hours with 300 ml of 2N sulfuric acid and 100 ml of glacial acetic acid while being stirred vigorously, is obtained. After extraction with ethyl acetate and washing with water, 10.9 g of 4-(4-chlorophenyl)-4-methyl-2-oxo-valeric acid is obtained as a red oil.

後処理

  1. temperaturewhile being cooled with ice within 20 minutes
  2. waitWithin 30 minutes
  3. customat 0° C
  4. waitAfter 20 hours at room temperature
  5. extractionit is extracted with ethyl acetate
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated by evaporation
  8. temperature13.8 g of acid, which is refluxed for 3 hours with 300 ml of 2N sulfuric acid and 100 ml of glacial acetic acid
  9. stirringwhile being stirred vigorously
  10. customis obtained
  11. extractionAfter extraction with ethyl acetate
  12. washwashing with water

出典と根拠

ORDレコード
ord-593610b77f2742aaa46dd4ac3161c77a
出典データセット
uspto-grants-2010_02
特許番号
US07662821B2

反応ノート

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