Hydrochloric Acid → (2,3,4,5-Tetrafluoro-6-methylphenyl)methanol

HRID 986687

反応式

HRID 986687 の反応式
F[C:2]1[C:7]([CH2:8][OH:9])=[C:6]([F:10])[C:5]([F:11])=[C:4]([F:12])[C:3]=1[F:13].O.Cl.O1CCC[CH2:17]1>>[CH3:17][C:2]1[C:3]([F:13])=[C:4]([F:12])[C:5]([F:11])=[C:6]([F:10])[C:7]=1[CH2:8][OH:9]

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 99232,3,4,5,6-Pentafluorobenzyl Alcohol

生成物 1

HCID 12943998(2,3,4,5-Tetrafluoro-6-methylphenyl)methanol

反応条件

温度
30 °C

実験手順

A solution of methyl bromide (9.6 g) in dry tetrahydrofuran (25 cm3) was added dropwise in a stirred mixture of magnesium turnings (5.0 g), dry tetrahydrofuran (50 cm3) and a small crystal of iodine at the ambient temperature (ca. 22° C.). When the addition was complete the mixture was stirred for a further 1 hour at the ambient temperature and the solution of methyl magnesium bromide thus formed was then added dropwise to a stirred solution to pentafluorobenzyl alcohol (17.8 g) in tetrahydrofuran (50 cm3) whilst the temperature was maintained at 30° C. When the addition was complete the mixture was stirred for a further 2 hours at the ambient temperature and for 3 hours at the reflux temperature. Water at 0° C. was added to the mixture, which was then acidified with dilute hydrochloric acid and extracted with diethyl ether (2×80 cm3). The extracts were combined, washed with water, dried over anhydrous magnesium sulphate and concentrated by evaporation of the solvent under reduced pressure. The residual oil (4.6 g) was shown by gas liquid chromatographic examination of a sample to consist of ca. 70% by weight of unreacted starting material and ca. 30% by weight of product. The oil was subjected to vigorous purification by column and thin-layer chromatography using a silica gel support and eluting with a mixture of diethyl ether and hexane (3:7 by volume), to obtain 2-methyl-3,4,5,6-tetrafluorobenzyl alcohol as a colourless oil.

後処理

  1. additionWhen the addition
  2. extractionextracted with diethyl ether (2×80 cm3)
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. concentrationconcentrated by evaporation of the solvent under reduced pressure
  6. customThe oil was subjected to vigorous purification by column and thin-layer chromatography
  7. washeluting with a mixture of diethyl ether and hexane (3:7 by volume)

出典と根拠

ORDレコード
ord-98d35c5e0b6a4886a52854dbf4bf941d
出典データセット
uspto-grants-1987_12
特許番号
US04714790

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