Isopropanol → HCID 66781497, compound

HRID 1096587Notes

Reaction equation

HRID 1096587 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:15]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:20]=CC=C[CH:16]=1.CC(O)C.C(OC(N=NC(OC(C)C)=O)=O)(C)C>C1COCC1>[CH:15]([O:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])([CH3:20])[CH3:16]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 87041Methyl 5-nitrosalicylate

Product 1

HCID 66781497HCID 66781497, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-hydroxy-5-nitrobenzoate (11.82 g, 60 mmol), triphenylphosphine (17.29 g, 66 mmol) and iPrOH (3.96 g, 5 ml, 66 mmol) were taken up in THF (150 ml) and cooled in ice. Di-isopropyl-azodicarboxylate (8.31 g, 10 ml, 66 mmol) was added carefully, and the reaction was stirred at RT overnight. The volatiles were removed in vacuo and the residue treated with EtOAc (50 ml). The solids that didn't dissolve were removed by filtration, and the filtrate evaporated to dryness in vacuo. The residue was purified by column chromatography to give methyl 2-isopropoxy-5-nitrobenzoate (6.92 g, 48.5%) as a yellow oil.

Workup

  1. temperaturecooled in ice
  2. customThe volatiles were removed in vacuo
  3. additionthe residue treated with EtOAc (50 ml)
  4. dissolutionThe solids that didn't dissolve
  5. customwere removed by filtration
  6. customthe filtrate evaporated to dryness in vacuo
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-86ad7b61e72249cf8d48ff898a9a9254
Source dataset
uspto-grants-2012_03
Patent number
US08138357B2

Reaction notes

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