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

HRID 1110448Notes

Reaction equation

HRID 1110448 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×

Procedure

A suspension of 63.18 g (0.39 mole) of Part (2) 5,8-dihydro-1,4-naphthalenediol in 300 ml of absolute ethanol was heated briefly until solution was achieved. To this hot stirred solution was added alternately in 5 portions a solution of 40 g (1 mole) of sodium hydroxide in 100 ml of water, and 120 g (89 ml=0.95 mole) of dimethyl sulfate. The heat evolved during the addition caused the solution to reflux. After the addition was complete (approx. 30 minutes), a solution of 10 g of sodium hydroxide in 20 ml of water was added and the mixture was heated overnight at 75°.

Workup

  1. temperaturewas heated briefly until solution
  2. additionThe heat evolved during the addition
  3. temperatureto reflux
  4. additionAfter the addition
  5. custom(approx. 30 minutes)
  6. temperaturethe mixture was heated overnight at 75°

Sources & evidence

ORD record
ord-eaf302a451d744ed9df6985040a799b1
Source dataset
uspto-grants-1990_12
Patent number
US04975461

Reaction notes

Loading…