Sodium Hydroxide → HCID 22419561, compound

HRID 1197397Notes

Reaction equation

HRID 1197397 reaction equation
[CH3:1][O:2][C:3]1[CH:38]=[CH:37][C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=2[O:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[C:12]([O:14]CC2C=CC(OC)=CC=2)=[O:13])=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=2[O:27][CH2:28][C:29]2[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=2)[C:12]([OH:14])=[O:13])=[CH:37][CH:38]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22419537HCID 22419537, compound

Product 1

HCID 22419561HCID 22419561, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

4-Methoxybenzyl 3,4-bis(4-methoxybenzyloxy)benzoate (6.48 g, 0.013 mol) was suspended in ethanol and treated with 2.5N aqueous sodium hydroxide solution (7.6 ml, 0.015 mol). The mixture was warmed to 60° C. for 4 h. The mixture was evaporated to low volume and then partitioned between water and ethyl acetate. The aqueous layer was washed again with ethyl acetate and then acidified and extracted into ethyl acetate. As the ethyl acetate solution was concentrated the product precipitated from solution and was filtered off to give the title compound (4.36 g, 87%).

Workup

  1. customThe mixture was evaporated to low volume
  2. custompartitioned between water and ethyl acetate
  3. washThe aqueous layer was washed again with ethyl acetate
  4. extractionextracted into ethyl acetate
  5. concentrationAs the ethyl acetate solution was concentrated the product
  6. customprecipitated from solution
  7. filtrationwas filtered off

Sources & evidence

ORD record
ord-7c7ffa5076654633bf1400db8453da9b
Source dataset
uspto-grants-1994_01
Patent number
US05275816

Reaction notes

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