4-Aminophenylacetic acid → HCID 14988368, compound

HRID 728559Notes

Reaction equation

HRID 728559 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[C:12]([C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:24]=1[OH:25])[C:19](Cl)=[O:20])([CH3:15])([CH3:14])[CH3:13]>COCCOC>[C:26]([C:23]1[CH:22]=[C:18]([CH:17]=[C:16]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:24]=1[OH:25])[C:19]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1)=[O:20])([CH3:29])([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 145334-Aminophenylacetic acidHCID 37871873,5-Di-tert-butyl-4-hydroxybenzoyl chloride

Product 1

HCID 14988368HCID 14988368, compoundYield 11.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A suspension of 9.2g (0.061 mole) of p-aminophenylacetic acid in 150 ml of 1,2-dimethoxyethane was added to a suspension of 8.0g (0.0298 mole) of 3,5-di-t-butyl-4-hydroxybenzoyl chloride in 100 ml of 1,2-dimethoxyethane, and the resulting mixture was stirred at room temperature for 12 hours. The reaction mixture was then filtered. The filtrate was thereafter diluted with water and chilled. The resulting precipitate was collected and recrystallized from a mixture of ethanol and water to give 1.32g of yellow crystalline 4-(3,5-di-t-butyl-4-hydroxybenzamido)phenylacetic acid, m.p. 253°-254° C. Analysis: Calculated for C23H29NO4 : %C, 72.0; %H, 7.6; %N, 3.6; Found: %C, 72.0; %H, 7.7; %N, 3.4.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. additionThe filtrate was thereafter diluted with water
  3. temperaturechilled
  4. customThe resulting precipitate was collected
  5. customrecrystallized from a mixture of ethanol and water

Sources & evidence

ORD record
ord-eb3e593b3df1426689f747cb1c887855
Source dataset
uspto-grants-1991_09
Patent number
US05049572

Reaction notes

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