Water → Methyl 3-(3-(2-quinolinylmethyloxy)phenoxymethyl)benzoate

HRID 2074018Notes

Reaction equation

HRID 2074018 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=1.[C:20](=[O:23])([O-])[O-].[K+].[K+].O.CN([CH:30]=[O:31])C>>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=1)[O:19][CH2:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[C:20]([O:31][CH3:30])=[O:23]

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 10988736Phenol, 3-(2-quinolinylmethoxy)-

Product 1

HCID 10111528Methyl 3-(3-(2-quinolinylmethyloxy)phenoxymethyl)benzoate

Conditions

Temperature
50 °C

Procedure

A mixture of 3-(2-quinolinylmethyloxy)phenol (2.51 g, 0.01 mol), 1.85 g (0.01 mol) of methyl 3-chloromethyl benzoate, and 1.5 g of potassium carbonate in 30 ml of DMF is heated at 50° C. overnight. The reaction mixture is poured into water, extracted with ethyl acetate and the organic solution separated, dried and evaporated to dryness. Recrystallization from ethyl acetate gives methyl 3-(3-(2-quinolinylmethyloxy)phenoxymethyl)benzoate. (M.P. 93°-94° C.)

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic solution separated
  3. customdried
  4. customevaporated to dryness
  5. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-f69239f6288e42bfa74f337ccae26342
Source dataset
uspto-grants-1990_04
Patent number
US04920132

Reaction notes

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