Hydrochloric Acid → HCID 16662682, compound

HRID 1925233Notes

Reaction equation

HRID 1925233 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]([CH:12]([CH2:18][CH3:19])[C:13]([O:15]CC)=[O:14])[CH:9]=[CH:10][CH:11]=1.[OH-].[Na+].Cl>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]([CH:12]([CH2:18][CH3:19])[C:13]([OH:15])=[O:14])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66875058HCID 66875058, compound

Product 1

HCID 16662682HCID 16662682, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of Ethyl 2-(3-(2,6-dimethylbenzyloxy)phenyl)-2-ethylacetate (Step C, 3.26 g, 10.0 mmol) in absolute ethanol (60 ml) was added 1N NaOH (20 ml) at room temperature. The reaction mixture was stirred for 3 hours, acidified by 1N HCl, and concentrated. The residue was taken into chloroform and washed with 1N HCl, 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.

Workup

  1. concentrationconcentrated
  2. washwashed with 1N HCl, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography on a silica gel column (chloroform:methanol 95:5 spiked with acetic acid)

Sources & evidence

ORD record
ord-f9f6fac531fa4914bc760c88405f59e3
Source dataset
uspto-grants-2012_05
Patent number
US08178675B2

Reaction notes

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