Hydrochloric Acid → HCID 16662682, compound

HRID 516850Notes

Reaction equation

HRID 516850 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)butanoate (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 to pH 3.5-4.0 by adding 1N HCl, and concentrated. The residue was taken into chloroform and washed with 0.1N 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 0.1N 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-1756672f6826429da2abd8dd3a3f9892
Source dataset
uspto-grants-2015_08
Patent number
US09115072B2

Reaction notes

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