Sodium Hydroxide → HCID 19004365, compound

HRID 2225830Notes

Reaction equation

HRID 2225830 reaction equation
C([O:3][C:4](=[O:35])[C:5](=[O:34])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([C:19]2[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:22]([OH:29])=[C:21]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:20]=2)=[O:18])=[CH:8][CH:7]=1)C.[OH-].[Na+]>CO>[CH3:28][C:25]([C:23]1[CH:24]=[C:19]([C:17](=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:9]2[CH:8]=[CH:7][C:6]([C:5](=[O:34])[C:4]([OH:35])=[O:3])=[CH:11][CH:10]=2)[CH:20]=[C:21]([C:30]([CH3:31])([CH3:32])[CH3:33])[C:22]=1[OH:29])([CH3:26])[CH3:27]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54099082HCID 54099082, compound

Product 1

HCID 19004365HCID 19004365, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As in example 10, a solution of 4-[5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-5-oxopentyloxy]-alpha-oxobenzeneacetic acid ethyl ester (0.8 g) in hot methanol (80 mL) was treated with 2N sodium hydroxide (1.75 mL) was stirred at room temperature for 75 minutes. The methanol was removed in vacuo, then the mixture was acidified with 3N hydrochloric acid and extracted with dichloromethane-tetrahydrofuran (2:1). The dried (MgSO4) extracts were evaporated and the solid residue was triturated from hexane, and then crystallized from acetone-hexane to provide 0.7 g of 4-[5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-5-oxopentyloxy]-alpha-oxobenzeneacetic acid, mp 144°-145° C.

Workup

  1. customThe methanol was removed in vacuo
  2. extractionextracted with dichloromethane-tetrahydrofuran (2:1)
  3. dry with materialThe dried (MgSO4) extracts
  4. customwere evaporated
  5. customthe solid residue was triturated from hexane
  6. customcrystallized from acetone-hexane

Sources & evidence

ORD record
ord-49785bf780334f4695828f6478afca5d
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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