4-Methylmorpholine → 4-Nitrophenol

HRID 1454984Notes

Reaction equation

HRID 1454984 reaction equation
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([Cl-]C([O-])=O)[CH:2]=1.C([O:21]C1C=CC(CO)=CC=1)C1C=CC=CC=1.CN1CCOCC1>ClCCl>[N+:7]([C:6]1[CH:5]=[CH:4][C:3]([OH:21])=[CH:2][CH:1]=1)([O-:9])=[O:8]

Participants

4

Reactant 2

HCID 79724-MethylmorpholineHCID 70043(4-(Benzyloxy)phenyl)methanol

Product 1

HCID 9804-Nitrophenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Nitrophenylchloroformate (260 g, 1.30 mmol) as a solution in 500 ml dichloromethane (DCM) is added to Wang resin (p-benzyloxybenzyl alcohol resin ex Calbiochem-Novabiochem, 350 g, 0.60 mmol) suspended in 1000 ml DCM and N-methylmorpholine (196 ml, 1.79 mmol) and stirred at room temperature for 18 hours. The resin is filtered and washed successively using methanol, DCM and ether to give WANG PARA-NITROPHENOL RESIN. [IR. 1761.5 cm−1; Loading 1.20 mmol/g].

Workup

  1. filtrationThe resin is filtered
  2. washwashed successively using methanol, DCM and ether

Sources & evidence

ORD record
ord-0bd1194d3d044624b689d3d65e4f2a42
Source dataset
uspto-grants-2009_01
Patent number
US07482347B2

Reaction notes

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