Ethanol → 5,8-dimethoxy-1,4-dihydronaphthalene

HRID 2286756Notes

Reaction equation

HRID 2286756 reaction equation
[C:1]1(O)[C:10]2[CH2:9][CH:8]=[CH:7][CH2:6][C:5]=2[C:4]([OH:11])=[CH:3][CH:2]=1.[OH-].[Na+].S([O:20][CH3:21])(OC)(=O)=O.[CH2:22](O)C>O>[CH3:22][O:11][C:4]1[C:5]2[CH2:6][CH:7]=[CH:8][CH2:9][C:10]=2[C:1]([O:20][CH3:21])=[CH:2][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6497Dimethyl SulfateHCID 14798Sodium Hydroxide2×HCID 765375,8-Dihydro-1,4-naphthalenediol

Product 1

HCID 117887505,8-dimethoxy-1,4-dihydronaphthalene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
75 °C

Procedure

A suspension of 63.18 g (0.39 mole) of 5,8-dihydro-1,4-naphthalenediol in 300 ml of absolute ethanol is heated briefly until solution is achieved. To this hot stirred solution is added alternately in five portions a solution of 40 g of sodium hydroxide in 100 ml of water, and 120 g of dimethyl sulfate. The heat evolved during the addition causes the solution to reflux. After the addition is complete a solution of 10 g of sodium hydroxide in 20 ml of water is added and the mixture is heated overnight at 75° C.

Workup

  1. temperatureis heated briefly until solution
  2. additionThe heat evolved during the addition
  3. temperatureto reflux
  4. additionAfter the addition
  5. additionis added

Sources & evidence

ORD record
ord-a86054add5be40df90fe569b6da6b5c8
Source dataset
uspto-grants-1981_05
Patent number
US04267373

Reaction notes

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