1-Propanethiol, sodium salt (1:1) → 4-Hydroxy-3-(3-methoxypropoxy)benzaldehyde

HRID 1690606Notes

Reaction equation

HRID 1690606 reaction equation
C[O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][C:4]=1[O:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16].C([S-])CC.[Na+]>CN(C=O)C>[OH:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][C:4]=1[O:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16]

Participants

4

Reactant 2

HCID 46817251-Propanethiol, sodium salt (1:1)HCID 112183584-Methoxy-3-(3-methoxypropoxy)benzaldehyde

Product 1

HCID 866332964-Hydroxy-3-(3-methoxypropoxy)benzaldehydeYield 97.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-methoxy-3-(3-methoxypropoxy)benzaldehyde (22 g, 98 mmol) was dissolved in DMF (490 mL) and sodium propanethiolate (12.5 g, 127 mmol) was added. The mixture was brought to 100° C. and the reaction mixture was stirred for 30 minutes. After cooling to room temperature, solvents were evaporated under reduced pressure and the residue was dissolved in dichloromethane (200 mL) and saturated aqueous ammonium chloride (200 mL). Hydrochloric acid 1N was then added until acidic pH. The organic layer was separated and washed with water and brine, dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure to yield 20 g (quantitative yield) of the desired product as a yellow oil, used in the next step without further purification.

Workup

  1. customwas brought to 100° C.
  2. customsolvents were evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane (200 mL)
  4. additionHydrochloric acid 1N was then added until acidic pH
  5. customThe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-afc3c28fb6b74f3fa4669e53b25e1d99
Source dataset
uspto-grants-2012_04
Patent number
US08153647B2

Reaction notes

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