Aluminum(III) Chloride → 4-Hydroxy-3-nitro-5-propoxybenzaldehyde

HRID 924985Notes

Reaction equation

HRID 924985 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:16][CH2:17][CH2:18][CH3:19])[C:11]=1[O:12]CCC)[CH:7]=[O:8])([O-:3])=[O:2].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[OH:12][C:11]1[C:10]([O:16][CH2:17][CH2:18][CH3:19])=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 86669352HCID 86669352, compound

Product 1

HCID 573549704-Hydroxy-3-nitro-5-propoxybenzaldehydeYield 97.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-nitro-4,5-dipropoxybenzaldehyde (153 mg, 0.573 mmol) in anhydrous CH2Cl2 (5 mL) was added anhydrous AlCl3 (151 mg, 1.15 mmol) at 0° C., after the addition, the reaction mixture was stirred at 50° C. for 1 hour. The reaction was quenched by water (20 mL), and the mixture was acidified with 2N aqueous HCl solution (20 mL), followed by a standard aqueous/EtOAc workup. Purification by column chromatography gave Intermediate 65 (126 mg, yield: 97.7%).

Workup

  1. additionafter the addition
  2. customThe reaction was quenched by water (20 mL)
  3. customPurification by column chromatography

Sources & evidence

ORD record
ord-ae3d7823d6e04c6a870184b7c42f43fd
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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