Sodium Hydroxide → HCID 19004300, compound

HRID 2225837Notes

Reaction equation

HRID 2225837 reaction equation
C([O:3][C:4](=[O:33])[C:5](=[O:32])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][S:16][C:17]2[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:20]([OH:27])=[C:19]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:18]=2)=[CH:8][CH:7]=1)C.[OH-].[Na+]>CO>[CH3:31][C:28]([C:19]1[CH:18]=[C:17]([S:16][CH2:15][CH2:14][CH2:13][O:12][C:9]2[CH:8]=[CH:7][C:6]([C:5](=[O:32])[C:4]([OH:33])=[O:3])=[CH:11][CH:10]=2)[CH:22]=[C:21]([C:23]([CH3:24])([CH3:25])[CH3:26])[C:20]=1[OH:27])([CH3:29])[CH3:30]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54396566HCID 54396566, compound

Product 1

HCID 19004300HCID 19004300, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As in Example 19, a solution of 4-[3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl] thio]propoxy]-alpha-oxobenzeneacetic acid ethyl ester (0.32 g) in methanol (15 mL) was treated with 2N sodium hydroxide (0.75 mL) was stirred at room temperature. After 3 hours, most of the methanol was removed in vacuo, then the mixture was acidified with 3N hydrochloric acid and extracted with dichloromethane-tetrahydrofuran (1:1). The dried (MgSO4) extracts were evaporated and the crude product was purified by flash chromatography over silica gel (toluene-ethyl acetate-acetic acid; 80:20:0.25 increasing to 74:25:1) to give 4-[3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]propoxy]-alpha-oxobenzeneacetic acid as an oil.

Workup

  1. custommost of the methanol was removed in vacuo
  2. extractionextracted with dichloromethane-tetrahydrofuran (1:1)
  3. dry with materialThe dried (MgSO4) extracts
  4. customwere evaporated
  5. customthe crude product was purified by flash chromatography over silica gel (toluene-ethyl acetate-acetic acid; 80:20:0.25 increasing to 74:25:1)

Sources & evidence

ORD record
ord-6c5215d9a7f14dca98491ef2f8e13ef5
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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