Dimethylformamide → HCID 12393621, compound

HRID 259008Notes

Reaction equation

HRID 259008 reaction equation
CN(C)[CH:3]=[O:4].[OH:6][C:7]1[C:16](COC)=[CH:15][CH:14]=[C:13]2[C:8]=1[CH2:9][CH2:10][CH2:11][C:12]2=O.[CH2:21](Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[C:29](=[O:32])([O-])[O-].[K+].[K+]>O>[CH2:21]([O:6][C:7]1[C:8]([CH2:9][O:4][CH3:3])=[C:13]2[C:14](=[CH:15][CH:16]=1)[C:29](=[O:32])[CH2:10][CH2:11][CH2:12]2)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 21425540HCID 21425540, compound

Product 1

HCID 12393621HCID 12393621, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 300 ml. of dimethylformamide are added 52 g. of 5-hydroxy-6-methoxymethyl-3,4-dihydro-1(2H)-naphthalenone, 32 g. of benzyl chloride and 35 g. of anhydrous potassium carbonate, and the mixture is stirred at 100° C for 4 hours. The reaction mixture is poured in 1 liter of water and the liberated oily layer is separated. To this layer is added 300 ml. of ethyl acetate and, after washing with water, the solution is dried over anhydrous sodium sulfate. The solvent is then distilled off under reduced pressure and the residue is recrystallized from hexane. The procedure provides 6-benzyloxy-5-methoxymethyl-3,4-dihydro-1(2H)-naphthalenone as colorless needles. Yield 58 g.; melting point; 55°-56° C.

Workup

  1. customthe liberated oily layer is separated
  2. additionTo this layer is added 300 ml
  3. washof ethyl acetate and, after washing with water
  4. dry with materialthe solution is dried over anhydrous sodium sulfate
  5. distillationThe solvent is then distilled off under reduced pressure
  6. customthe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-5a6fa0a3eff94547a5f17e86296115bd
Source dataset
uspto-grants-1977_07
Patent number
US04035512

Reaction notes

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