Sulfuric Acid → 2,5-Bishydroxymethyl-2',5'-dimethylbiphenyl

HRID 430882ノート

反応式

HRID 430882 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=1[C:15]1[CH:25]=[C:24]([C:26](OCC)=[O:27])[CH:23]=[CH:22][C:16]=1[C:17](OCC)=[O:18].S(=O)(=O)(O)O>C1COCC1>[OH:18][CH2:17][C:16]1[CH:22]=[CH:23][C:24]([CH2:26][OH:27])=[CH:25][C:15]=1[C:9]1[CH:10]=[C:11]([CH3:14])[CH:12]=[CH:13][C:8]=1[CH3:7]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 18676609Diethyl 2-(2',5'dimethylphenyl)terephthalateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 184199172,5-Bishydroxymethyl-2',5'-dimethylbiphenyl

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
67 °C

実験手順

LiAlH4 (7.9 g, 208 mmol) together with about 250 ml of THF were placed in a reaction vessel under a blanket of argon. Diethyl 2-(2′,5′dimethylphenyl)terephthalate (48.6 g, 149 mmol) (cf. C3) was diluted in a dropping funnel with about 60 ml of THF and slowly added dropwise. The reaction mixture was stirred vigorously during this addition. The mixture was diluted with another 100 ml of THF and then refluxed at 67° C. After 2 hours, it was cooled to RT. While cooling on a water bath and blanketing with argon, ice water was added dropwise until gas evolution had ceased. Dilute (10% strength) sulfuric acid was subsequently added dropwise until the turbid gray mixture became clear. The phase mixture was separated by addition of a generous amount of chloroform and the aqueous phase was subsequently shaken twice with chloroform. The organic phases were shaken once with H2O and evaporated. The crude product was recrystallized from chloroform/hexane: 24.7 g (68%) of colorless, microcrystalline powder; melting point: 145-148° C. (purity >95%).

後処理

  1. additionslowly added dropwise
  2. temperatureit was cooled to RT
  3. temperatureWhile cooling on a water bath
  4. additionwas added dropwise until gas evolution
  5. additionwas subsequently added dropwise until the turbid gray mixture
  6. customThe phase mixture was separated by addition of a generous amount of chloroform
  7. stirringthe aqueous phase was subsequently shaken twice with chloroform
  8. stirringThe organic phases were shaken once with H2O
  9. customevaporated
  10. customThe crude product was recrystallized from chloroform/hexane

出典と根拠

ORDレコード
ord-930c43e63c9541d4ad2c4a8b101bb869
出典データセット
uspto-grants-2001_11
特許番号
US06323373B1

反応ノート

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