Hydrochloric Acid → 2-Hydroxy-α-methyl-6-nitrobenzenemethanol

HRID 1611123Notes

Reaction equation

HRID 1611123 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[CH:4]=[O:5].[CH3:13][Al](C)C.Cl>>[OH:5][CH:4]([C:3]1[C:6]([N+:10]([O-:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=1[OH:1])[CH3:13]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 109539092-HYDROXY-6-NITROBENZALDEHYDEHCID 16682925Trimethylaluminum

Product 1

HCID 222589412-Hydroxy-α-methyl-6-nitrobenzenemethanolYield 95%

Procedure

To a stirred solution of 2-hydroxy-6-nitrobenzaldehyde (4.5 g, 26.926 mmol) was added dropwise trimethylaluminum (2M in toluene, 27 mL) under an argon atmosphere. The mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into a cold (0° C.) aqueous 1N hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=9/1) to give 2-(1-hydroxyethyl)-3-nitrophenol as an orange oil (4.660 g, yield; 95%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-790c751f41ae4185875ea2f541ad3702
Source dataset
uspto-grants-2006_01
Patent number
US06984649B1

Reaction notes

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