3-Nitrophenol → 1-Nitro-3-(2-phenylethoxy)benzene

HRID 1839423Notes

Reaction equation

HRID 1839423 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:11]1([CH2:21][CH2:22]O)[C:20]2[C:15](=CC=CC=2)[CH:14]=[CH:13][CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:22][CH2:21][C:11]2[CH:20]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 111373-NitrophenolHCID 11776TriphenylphosphineHCID 13047Naphthalen-1-ethanolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 130523131-Nitro-3-(2-phenylethoxy)benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 3-nitrophenol (1.39 g, 10 mmol), 1-naphthaleneethanol (1.89 g, 11 mmol), and triphenylphosphine (2.9 g, 11 mmol) in 100 ml of tetrahydrofuran was treated with a solution of 2.22 g (11 mmol) of diisopropylazodicarboxylate added dropwise. The resulting mixture was stirred overnight, and then concentrated and redissolved in a minimum amount of ethyl acetate. Purification on a silica gel column, eluting with 10% ethyl acetate in hexane, delivered 2.0 g of the ether.

Workup

  1. additionadded dropwise
  2. concentrationconcentrated
  3. dissolutionredissolved in a minimum amount of ethyl acetate
  4. customPurification on a silica gel column
  5. washeluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-6e4d62485c5f4b419059bb7e77bd3556
Source dataset
uspto-grants-2004_01
Patent number
US06677376B1

Reaction notes

Loading…