4-Hydroxybenzaldehyde → HCID 21841070, compound

HRID 1739412Notes

Reaction equation

HRID 1739412 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:13][CH2:14][CH2:15][S:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[C:17]1([S:16][CH2:15][CH2:14][CH2:13][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 24758Sodium hydrideHCID 2696063-Chloropropyl phenyl sulfide

Product 1

HCID 21841070HCID 21841070, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.69 g of 4-hydroxybenzaldehyde were dissolved in 30 ml of DMF, and the resultant solution was further added with 0.24 g of 60% NaH while cooling the solution with ice and then stirred for 1 hour after elevating the temperature of the solution to room temperature. Further, the solution was fed dropwise with 1.0 g of 1-chloro-3-phenylthio propane while cooling the solution with ice and then stirred for 1 hour at room temperature and further for a night at 50-60° C. After completed the reaction, the solution reacted was poured into ice-water and extracted with ethyl acetate. The organic layer resulted was then washed with aqueous solution of sodium hydroxide and dried with anhydrous magnesium sulfate, and the solvent used was removed by distillation under reduced pressure, thereby affording 1.2 g of 4-(3-phenylthiopropyloxy)-benzaldehyde.

Workup

  1. temperaturewhile cooling the solution with ice
  2. customto room temperature
  3. temperaturewhile cooling the solution with ice
  4. stirringstirred for 1 hour at room temperature and further for a night at 50-60° C
  5. customthe reaction
  6. customthe solution reacted
  7. extractionextracted with ethyl acetate
  8. customThe organic layer resulted
  9. washwas then washed with aqueous solution of sodium hydroxide
  10. dry with materialdried with anhydrous magnesium sulfate
  11. customthe solvent used was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-543005b2997143fd94378af7ac570ee1
Source dataset
uspto-grants-1999_10
Patent number
US05965743

Reaction notes

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