Hydroquinone → 4-(3,3-Dimethoxypropoxy)phenol

HRID 972117Notes

Reaction equation

HRID 972117 reaction equation
[Na].[C:2]1([CH:9]=[CH:8][C:6]([OH:7])=[CH:5][CH:4]=1)[OH:3].Cl[CH2:11][CH2:12][CH:13]([O:16][CH3:17])[O:14][CH3:15].[Cl-].[NH4+]>O.CN(C)C=O>[CH3:15][O:14][CH:13]([O:16][CH3:17])[CH2:12][CH2:11][O:3][C:2]1[CH:9]=[CH:8][C:6]([OH:7])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 25517Ammonium ChlorideHCID 142015Propane, 3-chloro-1,1-dimethoxy-HCID 5360545Sodium

Product 1

HCID 203966584-(3,3-Dimethoxypropoxy)phenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

The monosodium salt of hydroquinone (0.05 mole) and dimethylformamide (75 ml) are charged under nitrogen gas into a glass reaction vessel equipped with a mechanical stirrer, thermometer and addition funnel. The mixture is stirred until dissolved, and 1-chloro-3,3-dimethoxypropane (0.05 mole) is added dropwise over a period of about 20 minutes. After the addition is completed, the reaction mixture is heated at about 90° C. with stirring for a period of about 48 hours. After this time water (200 ml) is added, and the reaction mixture is carefully neutralized with ammonium chloride. The reaction mixture is then extracted with chloroform, and the organic phase is separated from the aqueous phase. The organic phase is then stripped of solvent, leaving an oil. This oil is distilled under reduced pressure to yield the desired product 4-(3,3-dimethoxypropoxy)phenol.

Workup

  1. customequipped with a mechanical stirrer
  2. additionthermometer and addition funnel
  3. dissolutionuntil dissolved
  4. additionAfter the addition
  5. stirringwith stirring for a period of about 48 hours
  6. extractionThe reaction mixture is then extracted with chloroform
  7. customthe organic phase is separated from the aqueous phase
  8. customleaving an oil
  9. distillationThis oil is distilled under reduced pressure

Sources & evidence

ORD record
ord-f1a77c61c2c74249ad3b7c541a81d9df
Source dataset
uspto-grants-1979_07
Patent number
US04163112

Reaction notes

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