2-Nitropropane → 3-Chloro-5-methylbenzaldehyde

HRID 1015944Notes

Reaction equation

HRID 1015944 reaction equation
[Na].[N+](C(C)C)([O-])=[O:3].[Cl:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([CH3:17])[CH:16]=1)[CH2:12]Br>C(O)C>[Cl:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([CH3:17])[CH:16]=1)[CH:12]=[O:3]

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 5360545SodiumHCID 123755491-(Bromomethyl)-3-chloro-5-methylbenzene

Product 1

HCID 107732013-Chloro-5-methylbenzaldehydeYield 42.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of sodium metal (52 mg, 2.3 mmol) in ethanol was added 2-nitropropane (0.23 g, 2.4 mmole) followed by the addition of 3-chloro-5-methylbenzylbromide (0.5 g, 2.3 mmol). The reaction was allowed to stir for 3 hours and the precipitate formed was filtered off. The filtrate was concentrated under reduced pressure, redissolved in diethylether and washed with 1N sodium hydroxide (twice), water, and dried over sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified via silica gel chromatography using 10% dichloromethane and 90% petroleum ether, to give 0.15 g of 3-chloro-5-methylbenzaldehyde (42%). 1H-NMR (CDCl3): 2.46 (s, 3H) 7.43(s, 1H) 7.56 (s, 1H) 7.68(s, 1H), 9.92 (s, 1H).

Workup

  1. customthe precipitate formed
  2. filtrationwas filtered off
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutionredissolved in diethylether
  5. washwashed with 1N sodium hydroxide (twice), water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe resulting residue was purified via silica gel chromatography

Sources & evidence

ORD record
ord-3c4098b73b3347798f86ed698a4fb4a0
Source dataset
uspto-grants-2011_07
Patent number
US07985762B2

Reaction notes

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