Methanol → Methyl 4-chlorophenylacetate

HRID 82406

反応式

HRID 82406 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:12]O>OS(O)(=O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 887MethanolHCID 15880(4-Chlorophenyl)acetic acid

生成物 1

HCID 104196Methyl 4-chlorophenylacetate収率 92%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid触媒

実験手順

A solution of 2-(4-chlorophenyl)acetic acid (20.0 g, 117 mmol) in dry methanol (235 mL) was treated with 5 drops of concentrated H2SO4 (cat.) at room temperature. The mixture was stirred overnight to completion and was concentrated in vacuo to about 40 mL. The concentrate was partitioned between an ether and half saturated NaHCO3 solution. The aqueous portion was back-extracted once with ether, and the organics were combined. The organic portion was washed with water, then brine, dried over MgSO4, and concentrated in vacuo. The material was placed under high vacuum for one hour to afford the pure methyl 2-(4-chlorophenyl)acetate as a pale yellow oil (19.8 g, 92%). 1H NMR (CDCl3, 400 MHz) δ 7.30 (d, J=8.4 Hz, 2H), 7.21 (d, J=8.4 Hz, 2H), 3.70 (s, 3H), 3.60 (2, 2H).

後処理

  1. concentrationwas concentrated in vacuo to about 40 mL
  2. customThe concentrate was partitioned between an ether and half saturated NaHCO3 solution
  3. extractionThe aqueous portion was back-extracted once with ether
  4. washThe organic portion was washed with water
  5. dry with materialbrine, dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. waitThe material was placed under high vacuum for one hour

出典と根拠

ORDレコード
ord-ab47ba45e4cd4ffdbfea4075d4713cef
出典データセット
uspto-grants-2014_09
特許番号
US08846681B2

関連ノート

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