Sulfuric Acid → 2-(Aminomethyl)-4-tert-butylphenol hydrochloride

HRID 437204ノート

反応式

HRID 437204 の反応式
[CH3:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[Cl:12]C[C:14]([NH:16]CO)=O.S(=O)(=O)(O)O>C(O)(=O)C.Cl.C(O)C.Cl>[ClH:12].[NH2:16][CH2:14][C:9]1[CH:10]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[CH:6]=[CH:7][C:8]=1[OH:11]

参加物

7

反応物 3

HCID 1118Sulfuric AcidHCID 73934-tert-ButylphenolHCID 62466N-Methylol-alpha-chloroacetamide

生成物 1

HCID 212969502-(Aminomethyl)-4-tert-butylphenol hydrochloride収率 51%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 313Hydrochloric Acid溶媒HCID 21887872Ethanol hydrochloride溶媒

反応条件

温度
20 °C

実験手順

A mixture of 4-(1,1-dimethylethyl)phenol (75 g., 0.50 mole), 2-chloro-N-(hydroxymethyl)acetamide (61 g., 0.50 mole) and 96% sulfuric acid (50 ml.) in acetic acid (500 ml.) is stirred at 20° C. for 4 hours and then poured into ice water (2 l.) providing a heterogenous mixture. After decanting the aqueous solution, the insoluble white gum is extracted with ether. The organic extract is washed with water and saturated brine and evaporated in vacuo leaving a residual oil. A solution of the latter in 12N hydrochloric acid-ethanol (1:1; 400 ml.) is heated at reflux for 4 hours, diluted with 12N hydrochloric acid (200 ml.) and slowly cooled to -20° C. The deposited white crystalline solid is collected to provide pure 2-aminomethyl-4-(1,1-dimethylethyl)phenol hydrochloride (55 g.), m.p. 227°-229° C. (dec.).

後処理

  1. customproviding a heterogenous mixture
  2. customAfter decanting the aqueous solution
  3. extractionthe insoluble white gum is extracted with ether
  4. extractionThe organic extract
  5. washis washed with water and saturated brine
  6. customevaporated in vacuo
  7. customleaving a residual oil
  8. temperatureat reflux for 4 hours
  9. temperatureslowly cooled to -20° C
  10. customThe deposited white crystalline solid is collected

出典と根拠

ORDレコード
ord-751b6ec5a68448adbd50f3abe781b226
出典データセット
uspto-grants-1977_06
特許番号
US04029816

反応ノート

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