Methanol → 1,1-Dimethoxy-1-(6-methoxy-2-naphthyl)propan-2-ol

HRID 1907005Notes

Reaction equation

HRID 1907005 reaction equation
Br[CH:2]([CH3:17])[C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=2)[CH:6]=1)=[O:4].[CH3:18][O-:19].[Na+].[OH2:21].[CH3:22]O>>[CH3:22][O:4][C:3]([O:19][CH3:18])([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=2)[CH:6]=1)[CH:2]([OH:21])[CH3:17]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 10942334Sodium MethoxideHCID 127563272-Bromo-1-(6-methoxynaphthalen-2-yl)propan-1-one

Product 1

HCID 113003471,1-Dimethoxy-1-(6-methoxy-2-naphthyl)propan-2-ol

Conditions

Temperature
15 °C

Procedure

A slurry of 22.5 g of 2-bromo-1-(6-methoxy-2-naphthyl)propan-1-one in 250 ml of methanol is cooled to 10° C. and treated with 9.7 g of sodium methoxide added as a solid over a period of about 10 minutes. The reaction mixture is stirred at 15° C. for about 10 minutes and allowed to warm to 20° C. at which temperature it is stirred for an additional 15 minutes. Then the reaction mixture is poured into 250 ml of water and extracted with 250 ml of methylene chloride. The organic layer is separated, filtered and dried over magnesium sulfate. Upon evaporation under reduced pressure, there is obtained 22 g of 1,1-dimethoxy-1-(6-methoxy-2-naphthyl)-propan-2-ol, as an oil.

Workup

  1. additionadded as a solid over a period of about 10 minutes
  2. temperatureto warm to 20° C. at which temperature it
  3. stirringis stirred for an additional 15 minutes
  4. extractionextracted with 250 ml of methylene chloride
  5. customThe organic layer is separated
  6. filtrationfiltered
  7. dry with materialdried over magnesium sulfate
  8. customUpon evaporation under reduced pressure

Sources & evidence

ORD record
ord-b232d33fc2dd4a61bc4e435362492ee4
Source dataset
uspto-grants-1987_03
Patent number
US04654438

Reaction notes

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