Benzene → HCID 131711335, compound

HRID 1704108Notes

Reaction equation

HRID 1704108 reaction equation
Br[CH:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[CH2:25]([O:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1C=CC=CC=1.C[O-].[Na+]>[I-].[K+].CO>[CH3:6][O:5][C:3](=[O:4])[CH:2]([O:39][C:36]1[CH:35]=[CH:34][C:33]([O:32][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:38][CH:37]=1)[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 7638MonobenzoneHCID 10942334Sodium MethoxideHCID 22761172HCID 22761172, compound

Product 1

HCID 131711335HCID 131711335, compoundYield 52.6%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 8.27 g of methyl bromo{p-[3-(p-chlorophenoxy)propoxy]phenyl}acetate, 5.0 g of p-benzyloxyphenol, 50 mg of potassium iodide, 10 ml of benzene and 40 ml of methanol is added 1.19 g of sodium methoxide. The mixture is refluxed for 24 hours and the solvent removed under reduced pressure. To the residue is added acetone and hexane and the solids filtered off. The filtrate is dried (MgSO4) and the solvent removed under reduced pressure. The residue is chromatographed over silica gel with dichloromethane as eluent. The oil obtained is crystallized from hexane-methanol to give 5.6 g of crystals. Recrystallization from methanol-ethyl acetate gives crystals, mp 98°-101° C.

Workup

  1. temperatureThe mixture is refluxed for 24 hours
  2. customthe solvent removed under reduced pressure
  3. additionTo the residue is added acetone and hexane
  4. filtrationthe solids filtered off
  5. dry with materialThe filtrate is dried (MgSO4)
  6. customthe solvent removed under reduced pressure
  7. customThe residue is chromatographed over silica gel with dichloromethane as eluent
  8. customThe oil obtained
  9. customis crystallized from hexane-methanol

Sources & evidence

ORD record
ord-33403066a79a42b2a01162791aa3a745
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

Loading…