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

HRID 35294

반응식

HRID 35294 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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°)).

후처리

  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

출처 및 근거

ORD 기록
ord-ad1bcaf341ee4060afdc32587a7a75af
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04766121

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