Sodium Hydroxide → 1,1'-[Oxybis(methylene)]bis(4-methoxybenzene)

HRID 1739125Notes

Reaction equation

HRID 1739125 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[OH-:11].[Na+]>CN(C)C=O.CCOCC>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][O:11][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 2211761,1'-[Oxybis(methylene)]bis(4-methoxybenzene)Yield 93%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Sordaricin benzyl ester (161.2 mg) was dissolved in 6 mL of N,N-dimethylformamide and p-methoxybenzyl chloride (1 mL) was added followed by excess sodium hydroxide (50 mg of a 60% dispersion in mineral oil). The mixture was stirred overnight. The mixture was diluted with ether and carefully washed with water. The ether layer was dried over anhydrous sodium sulfate and the volatiles removed in vacuo. The residue was purified by silica gel chromatography to give 192.5 mg (93%) of the p-methoxybenzyl ether.

Workup

  1. washcarefully washed with water
  2. dry with materialThe ether layer was dried over anhydrous sodium sulfate
  3. customthe volatiles removed in vacuo
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-bdfce936156d4504ad26e6171e394ebe
Source dataset
uspto-grants-1999_10
Patent number
US05965612

Reaction notes

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