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

HRID 1907011Notes

Reaction equation

HRID 1907011 reaction equation
[CH3:1][O-:2].[Na+].[Na].Br[CH:6]([CH3:21])[C:7]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[CH:10]=1)=[O:8].[C:22]1(C)C=CC=CC=1.[OH2:29]>CO>[CH3:1][O:2][C:7]([O:8][CH3:22])([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[CH:10]=1)[CH:6]([OH:29])[CH3:21]

Participants

7

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 5360545SodiumHCID 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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A sodium methoxide solution prepared by adding 3.2 g of sodium to 40 ml of methanol at 10° C. is added slowly to a solution of 20 g of 2-bromo-1-(6-methoxy-2-naphthyl)-propan-1-one in 100 ml of methanol, and 100 ml of toluene is added. The addition takes place over about a one-hour period and the reaction mixture is stirred and allowed to warm for 11/2 additional hours. Then the reaction mixture is poured into water, and extracted with toluene-ether. The organic phase is separated, dried and evaporated to afford 1,1-dimethoxy-1-(6-methoxy-2-naphthyl)propan-2-ol as an oil.

Workup

  1. additionis added
  2. additionThe addition
  3. temperatureto warm for 11/2 additional hours
  4. extractionextracted with toluene-ether
  5. customThe organic phase is separated
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-3df94ef5f1c3446f8fcd8d059da94a02
Source dataset
uspto-grants-1987_03
Patent number
US04654438

Reaction notes

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