Methanol → Methyl(p-cyanophenoxy){p-[3-(p-chlorophenoxy)propoxy]phenyl}acetate

HRID 1704110Notes

Reaction equation

HRID 1704110 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].CO.C[O-].[Na+].Br[CH:16]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][O:31][C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)=[CH:23][CH:22]=1)[C:17]([O:19][CH3:20])=[O:18]>C1C=CC=CC=1>[CH3:20][O:19][C:17](=[O:18])[CH:16]([O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH2:29][CH2:30][O:31][C:32]2[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=2)=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 130194-CyanophenolHCID 10942334Sodium MethoxideHCID 22761172HCID 22761172, compound

Product 1

HCID 131711336Methyl(p-cyanophenoxy){p-[3-(p-chlorophenoxy)propoxy]phenyl}acetateYield 41.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of 2.98 g of p-cyanophenol and 40 ml of methanol is added 1.19 g of sodium methoxide. To the mixture is added 8.22 g of methyl bromo{p-[3-(p-chlorophenoxy)propoxy]phenyl}acetate and 10 ml of benzene. The mixture is refluxed for 22 hours and the solvent removed under reduced pressure. The residue is chromatographed over silica gel with dichloromethane as the solvent. The product is obtained as an oil which is crystallized from methylcyclohexane-methanol and a small amount of hexane. Crystals are obtained and washed with hexane-methanol to give 3.7 g of white crystals, mp 102°-104° C.

Workup

  1. temperatureThe mixture is refluxed for 22 hours
  2. customthe solvent removed under reduced pressure
  3. customThe residue is chromatographed over silica gel with dichloromethane as the solvent
  4. customThe product is obtained as an oil which
  5. customis crystallized from methylcyclohexane-methanol
  6. customCrystals are obtained
  7. washwashed with hexane-methanol

Sources & evidence

ORD record
ord-fa22b5161bb148718ec6e1efc24cde04
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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