Sodium Hydroxide → alpha-[3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yloxy]phenylacetic Acid

HRID 1743225Notes

Reaction equation

HRID 1743225 reaction equation
[OH-].[Na+].[CH:3]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[C:16]3[C:17]([CH3:35])=[C:18]([O:23][CH:24]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:25]([O:27]C)=[O:26])[C:19]([CH3:22])=[C:20]([CH3:21])[C:15]=3[O:14][C:13]2([CH3:37])[CH3:36])=[CH:8][CH:7]=1)([CH3:5])[CH3:4]>O1CCCC1.CO>[CH:3]([C:6]1[CH:7]=[CH:8][C:9]([CH:12]2[C:16]3[C:17]([CH3:35])=[C:18]([O:23][CH:24]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:25]([OH:27])=[O:26])[C:19]([CH3:22])=[C:20]([CH3:21])[C:15]=3[O:14][C:13]2([CH3:37])[CH3:36])=[CH:10][CH:11]=1)([CH3:5])[CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10116253HCID 10116253, compound

Product 1

HCID 22238286alpha-[3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yloxy]phenylacetic AcidYield 27%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

An aqueous solution of 2 N sodium hydroxide (2.5 mL) was dropwise added to a solution of methyl α-[3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yloxy]phenylacetate (1.20 g, 2.54 mmol) in a mixture of tetrahydrofuran (24 mL) and methanol (6 mL), and the mixture was stirred for 30 minutes at room temperature. The reaction mixture was concentrated under reduced pressure, to which was added 2 N hydrochloric acid. Then, this was extracted twice with ethyl acetate. The organic layers were washed with water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was recrystallized from hexane to obtain the title compound (0.31 g, yield 27%), which was a mixture of diastereomers (ratio: 8/1).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, to which
  2. additionwas added 2 N hydrochloric acid
  3. extractionThen, this was extracted twice with ethyl acetate
  4. washThe organic layers were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was recrystallized from hexane

Sources & evidence

ORD record
ord-38c62536cdf643e8a3c3574808196a01
Source dataset
uspto-grants-2006_03
Patent number
US07008950B1

Reaction notes

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