Sodium Carbonate → 5-Methoxy-2-tetralone

HRID 1026778Notes

Reaction equation

HRID 1026778 reaction equation
[CH2:1]([NH-])[CH2:2][CH3:3].[OH2:5].[C:6]1([CH3:16])[CH:11]=[CH:10][C:9](S(O)(=O)=O)=[CH:8][CH:7]=1.[C:17]([O-])([O-])=[O:18].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH3:17][O:18][C:2]1[CH:1]=[CH:11][CH:10]=[C:9]2[C:3]=1[CH2:16][CH2:6][C:7](=[O:5])[CH2:8]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 23176953HCID 23176953, compound

Product 1

HCID 2591945-Methoxy-2-tetralone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 5-Methoxy-2-tetralone (X1) (150 g) in toluene (1000 mL) was prepared in a 2 L jacketed vessel equipped with a Dean-Stark condenser. To this solution was added propylamide (Y1) (150 g) and para-toluenesulfonic acid monohydrate (15 g). The mixture was refluxed for 24 hrs and reaction completion evaluated by hplc. The solution was cooled to 60° C. and 1% w/w Na2CO3 added (450 mL). In order to prevent product precipitation a further 300 mL of toluene was added. The phases were separated and the organic layer washed with water (450 mL). The organic layer was then cooled to 50° C. and aged to allow the product to crystallise. After crystallisation the slurry was further cooled to 5-10° C. and filtered. The filter cake was washed with toluene (2×150 mL), petroleum ether (150 mL) and the white crystalline needles were dried under vacuum at 25° C. to a constant weight of 124.4 g corresponding to compound (A2) (63.2% yield).

Workup

  1. customequipped with a Dean-Stark condenser
  2. temperatureThe mixture was refluxed for 24 hrs
  3. customreaction completion
  4. customproduct precipitation a further 300 mL of toluene
  5. additionwas added
  6. customThe phases were separated
  7. washthe organic layer washed with water (450 mL)
  8. temperatureThe organic layer was then cooled to 50° C.
  9. customto crystallise
  10. customAfter crystallisation the slurry
  11. temperaturewas further cooled to 5-10° C.
  12. filtrationfiltered
  13. washThe filter cake was washed with toluene (2×150 mL), petroleum ether (150 mL)

Sources & evidence

ORD record
ord-60d1d12e5bef400c8c9fa6fff0767660
Source dataset
uspto-grants-2014_05
Patent number
US08729306B2

Reaction notes

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