Hydrochloric Acid → HCID 16662683, compound

HRID 1925237Notes

Reaction equation

HRID 1925237 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]([CH2:12][CH:13]([CH3:19])[C:14]([O:16]CC)=[O:15])[CH:9]=[CH:10][CH:11]=1.[OH-].[Na+].Cl>C(O)C>[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]([CH2:12][CH:13]([CH3:19])[C:14]([OH:16])=[O:15])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67519647HCID 67519647, compound

Product 1

HCID 16662683HCID 16662683, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of Ethyl 3-(3-(2,6-dimethylbenzyloxy)phenyl)-2-methylpropanoate (Step C, 1.61 g, 4.9 mmol) in absolute ethanol (25 ml) was added 1N NaOH (10 ml) at room temperature. The reaction mixture was stirred for 3 hours, acidified to pH 3.5-4.0 by 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-e8a4c0533a3748f7b0376653c06d017c
Source dataset
uspto-grants-2012_05
Patent number
US08178675B2

Reaction notes

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