Aluminum(III) Chloride → HCID 57467383, compound

HRID 874180Notes

Reaction equation

HRID 874180 reaction equation
C[O:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([N+:16]([O-:18])=[O:17])[CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[OH:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([N+:16]([O-:18])=[O:17])[CH:4]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 13204948HCID 13204948, compound

Product 1

HCID 57467383HCID 57467383, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-(4-methoxy-2-nitrophenoxy)acetate 8 (1.0 g, 0.004 mol) in 10 mL dichloromethane cooled in an ice-bath was added aluminum chloride (1.6 g, 0.0133 mol) portion wise. The resulting mixture was gradually warmed to room temperature and then refluxed for 4 h. The progress of the reaction was monitored by thin layer chromatography (TLC). The reaction mixture was washed with saturated sodium bicarbonate solution and dried over sodium sulfate to give ethyl 2-(4-hydroxy-2-nitrophenoxy)acetate 9 which was purified by silica gel column chromatography using a gradient of hexane and ethyl acetate. White solid (0.28 g, 37%). 1H NMR (400 MHz, CDCl3): δ 1.26 (t, J=6.8 Hz, 3H); 4.27 (q, J=6.8 Hz, 2H); 4.71 (S, 2H); 6.32 (S, 1H); 6.90 (d, J=8.8 Hz, 1H); 6.99 (dd, J=3.2 Hz; 8.8 Hz, 1H); 7.30 (d, J=2.8 Hz, 1H).

Workup

  1. temperaturerefluxed for 4 h
  2. washThe reaction mixture was washed with saturated sodium bicarbonate solution
  3. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-d206fdea3c134097973b5a5a80cba468
Source dataset
uspto-grants-2015_03
Patent number
US08980883B2

Reaction notes

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