Sulfuric Acid → 6-tert-Butyl-4-chloro-m-cresol

HRID 910009

反応式

HRID 910009 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[C:10](O)([CH3:13])([CH3:12])[CH3:11].S(=O)(=O)(O)O.ClCCl>C(O)(=O)C>[C:10]([C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([CH3:9])=[CH:4][C:5]=1[OH:8])([CH3:13])([CH3:12])[CH3:11]

参加物

6

反応物 4

HCID 1118Sulfuric Acid2 回HCID 17324-Chloro-3-methylphenolHCID 6344DichloromethaneHCID 6386tert-Butanol2 回

生成物 1

HCID 356346-tert-Butyl-4-chloro-m-cresol

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
50 °C

実験手順

The starting compound 2-tert-butyl-4-chloro-5-methyl-phenol was prepared by t-butylation in the following manner: 4-chloro-3-methyl-phenol (10.0 g, 70 mmol) was dissolved in glacial acetic acid (30 mL) at ambient temperature. tert-Butanol (10.1 mL, 1.5 equivalents) was added, and subsequently 95% sulfuric acid (3.75 mL, 1 equiv.). The reaction vessel was closed with a drying tube and heated at 50° C. After 1 d, additional amounts of tert-butanol (5 mL) and sulfuric acid (1.8 mL) were added and heating was continued. After 3 d, dichlormethane (150 mL) was added, and the solution was washed three times with saturated aqueous sodium chloride (150 mL). Drying and evaporation of the solution provided 14.9 g of a pale yellow oil. Pure 2-tert-butyl-4-chloro-5-methyl-phenol was obtained by flash chromatography (silica/toluene-heptane 7:3) as a colourless oil, 1H NMR (CDCl3): δ 7.19 (s, 1H), 6.52 (s, 1H), 4.70 (s, 1H), 2.26 (s, 3H), 1.37 (s, 9H); TLC (silica/toluene-heptane 7:3) Rf=0.45.

後処理

  1. customThe reaction vessel was closed with a drying tube
  2. temperatureheating
  3. waitAfter 3 d
  4. washthe solution was washed three times with saturated aqueous sodium chloride (150 mL)
  5. customDrying
  6. customevaporation of the solution

出典と根拠

ORDレコード
ord-cd35efe3b2c1419386a39afba358f5ac
出典データセット
uspto-grants-2011_09
特許番号
US08022066B2

関連ノート

読み込み中…