Ammonia → 2-Methoxy-6-(trifluoromethyl)phenol

HRID 1088877

反応式

HRID 1088877 の反応式
C([Li])CCC.[F:6][C:7]([F:17])([F:16])[C:8]1[CH:9]=[C:10]([O:14][CH3:15])[CH:11]=[CH:12][CH:13]=1.B(OC)(OC)[O:19]C.N>CCCCCC.O1CCCC1.CN(C)CCN(C)C>[CH3:15][O:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:7]([F:16])([F:17])[F:6])[C:9]=1[OH:19]

参加物

8

反応物 4

HCID 222AmmoniaHCID 8470Trimethyl borateHCID 966913-(Trifluoromethyl)anisoleHCID 178418339Butyllithium

生成物 1

HCID 151333362-Methoxy-6-(trifluoromethyl)phenol

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8037N,N,N',N'-Tetramethylethylenediamine溶媒HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

A solution containing 160 ml of 1.6 molar butyllithium in hexane, 300 ml of tetrahydrofuran and 40 ml of N,N,N',N'-tetramethylethylenediamine was cooled to -78° C. and 43.3 g of 3-trifluoromethylanisole was added with stirring under nitrogen atmosphere. The solution was allowed to warm up to room temperature and cooled then again to -78° C. after which 35 ml of trimethyl borate was added. The solution was warmed up to 20° C. and 50 ml of conc. ammonia solution was added. The solvents were evaporated in reduced pressure and to the residue 60 ml of 98-100% formic acid followed with 25 ml of 35% hydrogen peroxide were added. The solution was extracted with ether-petroleum ether (1:1). The organic phase was separated and the product was extracted with 2.5 N NaOH-solution. The aqueous phase was acidified with hydrochloric acid and the product was extracted in dichloromethane. The solvent was removed for the most part in vacuo after which petroleum ether was added. The crystalline product was filtered, yield 8.5 g (18%), m.p. 51°-53° C.

後処理

  1. temperatureto warm up to room temperature
  2. temperaturecooled
  3. temperatureThe solution was warmed up to 20° C.
  4. customThe solvents were evaporated in reduced pressure and to the residue 60 ml of 98-100% formic acid
  5. additionwere added
  6. extractionThe solution was extracted with ether-petroleum ether (1:1)
  7. customThe organic phase was separated
  8. extractionthe product was extracted with 2.5 N NaOH-solution
  9. extractionthe product was extracted in dichloromethane
  10. customThe solvent was removed for the most part in vacuo after which petroleum ether
  11. additionwas added
  12. filtrationThe crystalline product was filtered

出典と根拠

ORDレコード
ord-5da80404712f44faa90d7573ab8ce473
出典データセット
uspto-grants-1990_10
特許番号
US04963590

関連ノート

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