Hydrochloric Acid → 4-Sulfanylbenzaldehyde

HRID 601581Notes

Reaction equation

HRID 601581 reaction equation
[Na].CC(S)(C)C.C[S:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1.Cl>CN(C)C=O>[SH:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 769854-(Methylthio)benzaldehydeHCID 450519182-Propanethiol, 2-methyl-, sodium salt

Product 1

HCID 109205784-SulfanylbenzaldehydeYield 38.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 2-methyl-2-propanethiol sodium salt (2.9 g, 26.3 mmol) and 4-(methylthio)benzaldehyde (2.0 g, 13.2 mmol) with dimethylformamide (40 mL) in a dry flask then heat at 160° C. for 4 hours. Cooled to room temperature, poured into 3N aqueous hydrochloric acid (400 mL) then extracted with dichloromethane (3×75 mL). The combined dichloromethane extracts were dried over sodium chloride/magnesium sulfate, filtered, and concentrated on a rotary evaporator to yield the crude product (3 g). The crude product was purified by flash column chromatography on silica gel eluting with ethyl acetate and hexanes to yield 4-mercapto-benzaldehyde (0.7 g): 1H NMR (DMSO-D6, 300.00 MHz): 9.9 (s, 1H), 7.7 (d, 2H), 7.5 (d, 2H).

Workup

  1. extractionthen extracted with dichloromethane (3×75 mL)
  2. dry with materialThe combined dichloromethane extracts were dried over sodium chloride/magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated on a rotary evaporator
  5. customto yield the crude product (3 g)
  6. customThe crude product was purified by flash column chromatography on silica gel eluting with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-c4b992bf5b2a49f6bb266a3fdb510268
Source dataset
uspto-grants-2011_03
Patent number
US07902372B2

Reaction notes

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