Methanol → HCID 131711333, compound

HRID 1704105Notes

Reaction equation

HRID 1704105 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].CO.Br[CH:21]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][O:36][C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=2)=[CH:28][CH:27]=1)[C:22]([O:24][CH3:25])=[O:23]>C1C=CC=CC=1>[CH3:25][O:24][C:22](=[O:23])[CH:21]([O:14][C:11]1[CH:10]=[CH:9][C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:13][CH:12]=1)[C:26]1[CH:27]=[CH:28][C:29]([O:32][CH2:33][CH2:34][CH2:35][O:36][C:37]2[CH:38]=[CH:39][C:40]([Cl:43])=[CH:41][CH:42]=2)=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 132544-PhenoxyphenolHCID 10942334Sodium MethoxideHCID 22761172HCID 22761172, compound

Product 1

HCID 131711333HCID 131711333, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a mixture of 4.66 g of p-phenoxyphenol, 1.19 g of sodium methoxide, 10 ml of benzene and 40 ml of methanol is added 8.27 g of methyl bromo{p-[3-(p-chlorophenoxy)propoxy]phenyl}acetate in 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 eluent giving a viscous oil which is again chromatographed over silica gel with dichloromethane as eluent. There is obtained 4.3 g of viscous oil which is crystallized from methylcyclohexane-methanol to give 3.6 g of white crystals, mp 78°-80° 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 eluent
  4. customgiving a viscous oil which
  5. customis again chromatographed over silica gel with dichloromethane as eluent

Sources & evidence

ORD record
ord-0d8cdfa9bba24b6d94871d8ba4758455
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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