p-Toluenesulfonic acid → 2-Propenoic acid, 3-(2-hydroxy-5-methylphenyl)-, ethyl ester

HRID 655068ノート

反応式

HRID 655068 の反応式
[CH2:1]([O:3][C:4](=[O:21])[CH:5]=[CH:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[O:14]C1CCCCO1)[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:1]([O:3][C:4](=[O:21])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[OH:14])[CH3:2]

参加物

4

反応物 2

HCID 6101p-Toluenesulfonic acidHCID 539559873-[5-Methyl-2-(tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid ethyl ester

生成物 1

HCID 153056922-Propenoic acid, 3-(2-hydroxy-5-methylphenyl)-, ethyl ester収率 71%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 193.7 g 3-[5-methyl-2-(tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid ethyl ester (Bunce, R., Moore, J., Org. Prep. Proc., 29(3), 293 (1997)) and 2 g p-toluenesulfonic acid in 2.5 l of ethanol was stirred at room temperature for 24 hours. Then the reaction mixture was concentrated and the residue was diluted with ether, washed with saturated sodium bicarbonate and brine, dried and evaporated to dryness. The resulting yellow solid was recrystallized to yield 97.7 g of colourless crystals.

後処理

  1. concentrationThen the reaction mixture was concentrated
  2. additionthe residue was diluted with ether
  3. washwashed with saturated sodium bicarbonate and brine
  4. customdried
  5. customevaporated to dryness
  6. customThe resulting yellow solid was recrystallized

出典と根拠

ORDレコード
ord-f9bd66031b74495f9115760ce39e80c9
出典データセット
uspto-grants-2011_12
特許番号
USRE043006E1

反応ノート

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