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

HRID 1666307

반응식

HRID 1666307 반응식
[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

참가 물질

5

반응물 3

HCID 7969ThiophenolHCID 14797Potassium Hydroxide2회HCID 19010509Methyl 2-(3,5-dimethoxyphenyl)-2-bromoacetate

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c0f83d0188c544b68f7c740523548e2f
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044067B2

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