Dimethyl Sulfate → HCID 21429243, compound

HRID 437596Notes

Reaction equation

HRID 437596 reaction equation
[C:1]1(=[O:8])[CH:6]=[CH:5][C:4](=[O:7])[CH:3]=[CH:2]1.[CH:9]1[CH2:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+].S(OC)(O[CH3:20])(=O)=O.C1C=CC2C(=CC=CC=2O)C=1>O>[CH3:20][O:7][C:4]1[C:5]2[CH:13]3[CH2:9][CH:10]([CH:11]=[CH:12]3)[C:6]=2[C:1]([OH:8])=[CH:2][CH:3]=1

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 70051-NaphtholHCID 14798Sodium HydroxideHCID 21429234HCID 21429234, compound

Product 1

HCID 21429243HCID 21429243, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Adduct (VII) (34.8 g.) was added to a solution of 32 g. NaOH in 200 ml. water. The solution was stirred and 30.8 g. dimethyl sulfate added dropwise, giving a mild exotherm. Stirring was continued at room temperature for 3 hours. Then, the mixture was filtered, acidified with concentrated HCl, and extracted with chloroform. The organic layer was dried and evaporated to give a viscous brown oil. Distillation gave 6.1 g. of naphthol (VIII) as a thick yellow, viscous liquid, b. 178° C./0.1 mm.

Workup

  1. customgiving a mild exotherm
  2. stirringStirring
  3. filtrationThen, the mixture was filtered
  4. extractionextracted with chloroform
  5. customThe organic layer was dried
  6. customevaporated
  7. customto give a viscous brown oil
  8. distillationDistillation
  9. customgave 6.1 g
  10. custom178° C./0.1 mm

Sources & evidence

ORD record
ord-1822b53e35134422b631c18105354233
Source dataset
uspto-grants-1977_06
Patent number
US04031237

Reaction notes

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