Thiophenol → 2-(3,5-Dimethoxyphenyl)-2-(phenylsulfanyl)acetic acid

HRID 1666307

反応式

HRID 1666307 の反応式
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:20](Br)[C:21]([O:23]C)=[O:22])[CH:15]=[C:16]([O:18][CH3:19])[CH:17]=1>O1CCOCC1>[CH3:19][O:18][C:16]1[CH:15]=[C:14]([CH:20]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:21]([OH:23])=[O:22])[CH:13]=[C:12]([O:11][CH3:10])[CH:17]=1

参加物

5

反応物 3

HCID 7969ThiophenolHCID 14797Potassium Hydroxide2 回HCID 19010509Methyl 2-(3,5-dimethoxyphenyl)-2-bromoacetate

生成物 1

HCID 670817982-(3,5-Dimethoxyphenyl)-2-(phenylsulfanyl)acetic acid

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
80 °C

実験手順

A mixture of benzenethiol (5.91 g) and potassium hydroxide (3.48 g) in dioxane (200 ml) was heated at 80° C. for one hour under nitrogen. After cooling down to 20° C., a solution of methyl 2-(3,5-dimethoxyphenyl)-2-bromoacetate (15.0 g) in dioxane (100 ml) was added and the mixture was refluxed for two hours. Additionally potassium hydroxide (1.5 g) was added and the reflux continued for further two hours. After cooling to room temperature, the suspension was filtered and the filtrate concentrated to dryness. The residue was partitioned between dichloromethane (300 ml) and aqueous hydrochloric acid (1M, 300 ml). The organic phase was dried and concentrated to dryness, leaving crude 2-(3,5-dimethoxyphenyl)-2-(phenylsulfanyl)acetic acid. Crystallization from diethyl ether gave the pure compound (7.2 g), m.p. 124-126° C.

後処理

  1. temperatureAfter cooling down to 20° C.
  2. temperaturethe mixture was refluxed for two hours
  3. temperatureAfter cooling to room temperature
  4. filtrationthe suspension was filtered
  5. concentrationthe filtrate concentrated to dryness
  6. customThe residue was partitioned between dichloromethane (300 ml) and aqueous hydrochloric acid (1M, 300 ml)
  7. customThe organic phase was dried
  8. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-c0f83d0188c544b68f7c740523548e2f
出典データセット
uspto-grants-2011_10
特許番号
US08044067B2

関連ノート

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