Water → HCID 14627830, compound

HRID 1030236Notes

Reaction equation

HRID 1030236 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[S:13][CH:14]=[C:15]([CH2:17][C:18]([O:20]CC)=[O:19])[N:16]=2)[CH:8]=[C:7]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:6]=1[OH:27])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O>C(O)C>[C:1]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[S:13][CH:14]=[C:15]([CH2:17][C:18]([OH:20])=[O:19])[N:16]=2)[CH:8]=[C:7]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:6]=1[OH:27])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 14627819HCID 14627819, compound

Product 1

HCID 14627830HCID 14627830, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,6-Di-tert-butyl-4-[(4-ethoxycarbonylmethyl-2-thiazolyl)oxy]phenol (produced in Example 41) (0.40 g) was dissolved in 15 ml of ethanol, 8 ml of 2 N aqueous sodium hydroxide was added to the solution at room temperature, and the mixture was stirred for 1 hour. The reaction mixture was poured into water and, after acidification to Congo red with 36% hydrochloric acid, extracted with dichloromethane. The organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated. The crude product obtained was washed with diethyl ether-hexane (1:10) to give 0.30 g of the desired compound as a colorless solid.

Workup

  1. extractionafter acidification to Congo red with 36% hydrochloric acid, extracted with dichloromethane
  2. washThe organic layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product obtained
  6. washwas washed with diethyl ether-hexane (1:10)

Sources & evidence

ORD record
ord-af15d0ed471c4e669532a10e0c751eb3
Source dataset
uspto-grants-1992_04
Patent number
US05104889

Reaction notes

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