Water → HCID 12531891, compound

HRID 1863338Notes

Reaction equation

HRID 1863338 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C[O-].[Na+].Br[CH:13]([C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:27][CH:26]=2)=[CH:20][CH:19]=1)[C:14]([O:16][CH3:17])=[O:15].O>C1C=CC=CC=1.[I-].[K+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:13]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:26]=[CH:27][C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:29][CH:30]=3)=[CH:20][CH:19]=2)[C:14]([O:16][CH3:17])=[O:15])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 46844-ChlorophenolHCID 10942334Sodium MethoxideHCID 20392606HCID 20392606, compound

Product 1

HCID 12531891HCID 12531891, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 241BenzeneSolvent

Procedure

To a solution of 3.21 g of p-chlorophenol, 1.19 g of sodium methoxide and 50 mg of potassium iodide was added 7.54 g of methyl α-bromo-α-[p-(p-tert-butylphenoxy)phenyl]acetate in 10 ml of benzene. The mixture was refluxed overnight and cooled to room temperature. The mixture was then poured into 100 ml of water and extracted with 2×75 ml of ether. The combined extracts were washed with 50 ml of 5% NaOH, 2×50 ml of water, 50 ml saturated brine and dried (MgSO4). Evaporation of the solvent yielded an amber oil. Chromatography on 100 g of silica gel (benzene) afforded 7.36 g of product as a pale yellow glass.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. extractionextracted with 2×75 ml of ether
  3. washThe combined extracts were washed with 50 ml of 5% NaOH, 2×50 ml of water, 50 ml saturated brine
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent
  6. customyielded an amber oil

Sources & evidence

ORD record
ord-d49e3de0c48d4b96b8c80a77d6e3cca3
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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