2-Chloro-1,3-dimethyl-5-nitrobenzene → HCID 18614245, compound

HRID 1265153Notes

Reaction equation

HRID 1265153 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:17])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Cl[C:25]1[C:30]([CH3:31])=[CH:29][C:28]([N+:32]([O-:34])=[O:33])=[CH:27][C:26]=1[CH3:35]>CS(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[O:17][C:25]1[C:26]([CH3:35])=[CH:27][C:28]([N+:32]([O-:34])=[O:33])=[CH:29][C:30]=1[CH3:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 99205692-Chloro-1,3-dimethyl-5-nitrobenzeneHCID 135310983-(Benzyloxy)-4-methoxyphenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 18614245HCID 18614245, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-benzyloxy-4-methoxyphenol (3 g) in DMSO (2 mL) was added potassium t-butoxide (1.6 g). After 30 min, 4-chloro-3,5-dimethylnitrobenzene (2 g) was added and the resulting solution was heated at 80° C. for 2 h. The reaction mixture was partitioned between ethyl acetate and 1N aqueous NaOH, and the organic layer was washed with water, brine, dried over sodium sulfate and concentrated in vacuo to afford 4-(3-benzyloxy-4-methoxyphenoxy)-3,5-dimethylnitrobenzene (1.9 g) as an orange solid.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and 1N aqueous NaOH
  2. washthe organic layer was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-47233e73d064459d928cd10d2e5e0821
Source dataset
uspto-grants-2003_04
Patent number
US06545018B2

Reaction notes

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