4-Nitrobenzoic Acid → 4-(Methoxycarbonyl)-4-methylcyclohexyl 4-nitrobenzoate

HRID 1504037Notes

Reaction equation

HRID 1504037 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][C:5]([CH3:12])([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:3]1.[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[N+:13]([C:16]1[CH:17]=[CH:18][C:19]([C:20]([O:1][CH:2]2[CH2:3][CH2:4][C:5]([C:8]([O:10][CH3:11])=[O:9])([CH3:12])[CH2:6][CH2:7]2)=[O:21])=[CH:23][CH:24]=1)([O-:15])=[O:14]

Participants

6

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 13236236Methyl 4-hydroxy-1-methylcyclohexane-1-carboxylate

Product 1

HCID 866951964-(Methoxycarbonyl)-4-methylcyclohexyl 4-nitrobenzoateYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-hydroxy-1-methylcyclohexane-1-carboxylate (5.8 g, 33.68 mmol, 1.00 equiv) and 4-nitrobenzoic acid (11.26 g, 67.38 mmol, 2.00 equiv) in 80 mL of anhydrous THF was added PPh3 (17.67 g, 67.37 mmol, 2.00 equiv) at room temperature. Then DIAD (13.62 g, 67.36 mmol, 2.00 equiv) was added dropwise and the resulting solution was stirred for 2 h at room temperature. The reaction was quenched water, extracted with 3×150 mL of ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/50) to give 4-(methoxycarbonyl)-4-methylcyclohexyl 4-nitrobenzoate (5.5 g, 51%) as a white solid.

Workup

  1. customThe reaction was quenched water
  2. extractionextracted with 3×150 mL of ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-127f981b3e95452d842c2f4ec43dde78
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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