Methanol → HCID 53649059, compound

HRID 1979517Notes

Reaction equation

HRID 1979517 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH3:18])([CH3:17])[CH2:9][CH2:8]1)=[O:6].[CH3:19]I.CO>O1CCCC1.O>[CH3:3][O:4][C:5]([C:7]1([CH3:19])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH3:18])([CH3:17])[CH2:9][CH2:8]1)=[O:6]

Participants

7

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53905941HCID 53905941, compound

Product 1

HCID 53649059HCID 53649059, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

5.7 g of sodium hydride are placed in 80 ml of absolute tetrahydrofuran in a 500 ml flask provided with a thermometer, stirrer, reflux condenser and dropping funnel and 43.6 g of 1,1-dimethyl-tetralin-4-carboxylic acid methyl ester are added dropwise thereto. The mixture is then heated at reflux temperature for 1 hour. After cooling, 34 g of methyl iodide in 80 ml of absolute tetrahydrofuran are added dropwise and the mixture is held at reflux temperature for a further 1 hour. After cooling, a small amount of methanol is added, the mixture is poured into water and extracted with ether. The ether extracts are washed neutral, dried and evaporated. Distillation gives a quantitative yield of 1,1,4-trimethyl-tetralin-4-carboxylic acid methyl ester of boiling point 102° C./1.5 mmHg; nD20 =1.5219. Odour: tobacco, similar to (3).

Workup

  1. customprovided with a thermometer, stirrer
  2. temperaturereflux condenser
  3. temperatureThe mixture is then heated
  4. temperatureat reflux temperature for 1 hour
  5. temperatureAfter cooling
  6. temperatureat reflux temperature for a further 1 hour
  7. temperatureAfter cooling
  8. extractionextracted with ether
  9. washThe ether extracts are washed neutral
  10. customdried
  11. customevaporated
  12. distillationDistillation

Sources & evidence

ORD record
ord-60e63df463834eca9c6ceccbd8c655dd
Source dataset
uspto-grants-1984_11
Patent number
US04481133

Reaction notes

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