4-Bromoanisole → 1-(5-Hydroxy-2-methoxyphenyl)-1-(4-methoxy-phenyl)-methanol

HRID 346335

反応式

HRID 346335 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[Mg].[OH:11][C:12]1[CH:13]=[CH:14][C:15]([O:20][CH3:21])=[C:16]([CH:19]=1)[CH:17]=[O:18].[Cl-].[NH4+]>O1CCCC1>[OH:11][C:12]1[CH:13]=[CH:14][C:15]([O:20][CH3:21])=[C:16]([CH:17]([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)[OH:18])[CH:19]=1

参加物

6

反応物 4

HCID 77304-BromoanisoleHCID 25517Ammonium ChlorideHCID 3583415-Hydroxy-2-MethoxybenzaldehydeHCID 5462224Magnesium

生成物 1

HCID 150239551-(5-Hydroxy-2-methoxyphenyl)-1-(4-methoxy-phenyl)-methanol収率 99.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To the Grignard reagent prepared from 4-bromoanisole (286 g) and magnesium turnings (38.5 g) in dry tetrahydrofuran (480 ml) was added, dropwise, with vigorous stirring, a solution of 5-hydroxy-2-methoxybenzaldehyde (100 g) in dry tetrahydrofuran (1 liter). The mixture was heated on a steam bath for 3 hours, cooled and decomposed with saturated ammonium chloride solution. The organic layer was removed and the aqueous extracted with ethyl acetate (twice). The combined organics were washed with water, dried with anhydrous magnesium sulphate and evaporated to dryness. The residue was stirred with water (4 liters), and the buff coloured solid collected and dried to give crude 1-(5-hydroxy-2-methoxyphenyl)-1-(4-methoxy- phenyl)-methanol (170 g, 99%), m.p. 62-68°. This carbinol (85 g) was dissolved in ethanol (700 ml) and 10% palladium on charcoal (10 g) added. The mixture was hydrogenated in a Parr apparatus at 45° until hydrogen uptake ceased. The mixture was filtered, the filtrate evaporated to dryness and the residue filtered through a column containing silica gel, eluting with dichloromethane, to give 2,4'-dimethoxy-5-hydroxydiphenylmethane (46 g, 58%), m.p. 56-58° (from petroleum spirit (60-80°)).

後処理

  1. additionwas added
  2. temperatureThe mixture was heated on a steam bath for 3 hours
  3. temperaturecooled
  4. customThe organic layer was removed
  5. extractionthe aqueous extracted with ethyl acetate (twice)
  6. washThe combined organics were washed with water
  7. dry with materialdried with anhydrous magnesium sulphate
  8. customevaporated to dryness
  9. customcollected
  10. customdried

出典と根拠

ORDレコード
ord-53205856fe6c43d68dde8c39786172d7
出典データセット
uspto-grants-1991_10
特許番号
US05061798

関連ノート

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