Ethyl Acetate → (R)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetate

HRID 1053605ノート

反応式

HRID 1053605 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:12])[C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:13](OCC)(=O)C>CO.S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:12])[C:9]([O:11][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 8857Ethyl AcetateHCID 2733127(R)-2-(3-Chlorophenyl)-2-hydroxyacetic acid

生成物 1

HCID 15606324(R)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetate収率 93%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1118Sulfuric Acid溶媒

実験手順

A solution of (R)-2-(3-chlorophenyl)-2-hydroxyacetic acid (25 g, 133.69 mmol, 1.00 equiv.) in methanol (300 mL) and sulfuric acid (3 mL) was heated at reflux for about 16 hours, and then concentrated in vacuo. After the solution was poured into a water/ice mixture (200 mL), the pH value of the solution was adjusted to 9 with sodium carbonate. Standard extractive workup with ethyl acetate (2×100 mL), gave the title product as an off-white solid (24.8 g; yield=93%). 1H NMR (300 MHz, CDCl3) δ: 7.45 (s, 1H), 7.32 (m, 3H), 5.17 (d, J=4.5 Hz, 1H), 3.80 (s, 3H).

後処理

  1. temperatureat reflux for about 16 hours
  2. concentrationconcentrated in vacuo
  3. additionAfter the solution was poured into a water/ice mixture (200 mL)

出典と根拠

ORDレコード
ord-6508dbc1be154d08bb7661b8aa764d13
出典データセット
uspto-grants-2016_07
特許番号
US09394239B2

反応ノート

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