Water → 2-Aminomethyl-4-(1,1-dimethylpropyl)phenol hydrochloride

HRID 437208

反応式

HRID 437208 の反応式
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([CH3:5])[CH2:3][CH3:4].[Cl:13]C[C:15]([NH:17]CO)=O.O>C(O)(=O)C.S(=O)(=O)(O)O.C(O)C>[ClH:13].[NH2:17][CH2:15][C:10]1[CH:11]=[C:6]([C:2]([CH3:1])([CH3:5])[CH2:3][CH3:4])[CH:7]=[CH:8][C:9]=1[OH:12]

参加物

7

反応物 3

HCID 962WaterHCID 66434-tert-PentylphenolHCID 62466N-Methylol-alpha-chloroacetamide

生成物 1

HCID 214307652-Aminomethyl-4-(1,1-dimethylpropyl)phenol hydrochloride収率 37%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒HCID 1118Sulfuric Acid溶媒

実験手順

A mixture of 4-(1,1-dimethylpropyl)phenol (32.8 g., 0.2 mole) and 2-chloro-N-(hydroxymethyl)acetamide (24.6 g., 0.2 mole) in acetic acid (200 ml.) and 96% sulfuric acid (20 ml.) is stirred at 20° for 12 hours and then poured into cold water (1 l.). The solid that separates is extracted with ether and the ether extract is washed with water and salt brine and evaporated to dryness. The oily residue is dissolved in a mixture of 12N hydrochloric acid (100 ml.) and ethanol (100 ml.). The mixture is refluxed for 7 hours. The mixture then is evaporated to dryness under reduced pressure. The residue is triturated with dry ether to obtain a sticky white solid that is dissolved in hot ethanol (50 ml.) and precipitated in the cold by addition of ether (800 ml.). The solid is then crystallized from ethanol - 12N hydrochloric acid (1:10) to obtain 2-aminomethyl-4-(1,1-dimethylpropyl)phenol hydrochloride (17 g.), m.p. 191°-192° C.

後処理

  1. extractionThe solid that separates is extracted with ether
  2. extractionthe ether extract
  3. washis washed with water and salt brine
  4. customevaporated to dryness
  5. dissolutionThe oily residue is dissolved in a mixture of 12N hydrochloric acid (100 ml.) and ethanol (100 ml.)
  6. temperatureThe mixture is refluxed for 7 hours
  7. customThe mixture then is evaporated to dryness under reduced pressure
  8. customThe residue is triturated with dry ether
  9. customto obtain a sticky white solid
  10. customprecipitated in the
  11. additioncold by addition of ether (800 ml.)
  12. customThe solid is then crystallized from ethanol - 12N hydrochloric acid (1:10)

出典と根拠

ORDレコード
ord-58f4e069bd2b448db2e5a3b73255a3ee
出典データセット
uspto-grants-1977_06
特許番号
US04029816

関連ノート

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