Sodium Hydroxide → HCID 19004314, compound

HRID 2225791Notes

Reaction equation

HRID 2225791 reaction equation
C[O:2][C:3](=[O:32])[C:4](=[O:31])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]#[C:14][C:15]2[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:22][O:23][C:24](=[O:30])[C:25]([CH3:29])([CH3:28])[CH2:26][CH3:27])=[CH:7][CH:6]=1.[OH-].[Na+]>CO>[CH3:28][C:25]([CH3:29])([CH2:26][CH3:27])[C:24](=[O:30])[O:23][CH2:22][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([CH3:21])[C:15]=1[C:14]#[C:13][CH2:12][O:11][C:8]1[CH:7]=[CH:6][C:5]([C:4](=[O:31])[C:3]([OH:32])=[O:2])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53676059HCID 53676059, compound

Product 1

HCID 19004314HCID 19004314, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-[3-[2-[(2,2-dimethyl-1-oxobutoxy)methyl]-6-methylphenyl]-2-propynyloxy]-alpha-oxobenzeneacetic acid methyl ester (1.25 g) in methanol (5 mL) was treated with 3N sodium hydroxide solution (1.25 mL) and the mixture was stirred for 5 minutes at room temperature. Most of the methanol was removed under reduced pressure, and the concentrate was partitioned between diethyl ether (25 mL,) and water (25 mL). The separated aqueous layer was acidified with 1N hydrochloric acid (5 mL) and extracted with diethyl ether (2×50 mL). The combined organic phases were washed with brine, dried (Na2SO4) and evaporated in vacuo to give 1.13 g of 4-[3-[2-[(2,2-dimethyl-1-oxobutoxy)methyl]-6-methylphenyl]-2-propynyloxy]-alphaoxobenzeneacetic acid as a colorless oil.

Workup

  1. customMost of the methanol was removed under reduced pressure
  2. customthe concentrate was partitioned between diethyl ether (25 mL,) and water (25 mL)
  3. extractionextracted with diethyl ether (2×50 mL)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-73bff77d43db4ef58a9fdb50d3130ea1
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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