Sodium Hydroxide → HCID 44547164, compound

HRID 73445Notes

Reaction equation

HRID 73445 reaction equation
[CH3:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:14][C:15]([O:17]CC)=[O:16])[CH:9]=[CH:10][C:11]=1[O:12][CH3:13].[OH-].[Na+]>C(O)C>[CH3:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:2]([CH3:1])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:14][C:15]([OH:17])=[O:16])[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66874928Ethyl 2-(3-(2,6-dimethylbenzyloxy)-4-methoxyphenyl)acetate

Product 1

HCID 44547164HCID 44547164, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of Ethyl 2-(3-(2,6-dimethylbenzyloxy)-4-methoxyphenyl)acetate (Step B, 7.86 g, 24 mmol) in absolute ethanol (120 ml) was added 1N NaOH (50 ml) at room temperature. The reaction mixture was stirred for 3 hours, or until all the starting material is gone, concentrated and diluted with chloroform and acidified by 1M HCl to bring the pH to 3.5-4. The organic layer was washed with brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (chloroform:methanol 95:5 spiked with acetic acid) to give the title compound as a white solid.

Workup

  1. concentrationconcentrated
  2. additiondiluted with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography on a silica gel column (chloroform:methanol 95:5 spiked with acetic acid)

Sources & evidence

ORD record
ord-e0070d49eefb4b3f98e5c5f4d8254d38
Source dataset
uspto-grants-2014_09
Patent number
US08829058B2

Reaction notes

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