4-Aminobenzoic Acid → R 8605

HRID 728557Notes

Reaction equation

HRID 728557 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[C:11]([C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:23]=1[OH:24])[C:18](Cl)=[O:19])([CH3:14])([CH3:13])[CH3:12]>COCCOC>[C:6]([C:5]1[CH:9]=[CH:10][C:2]([NH:1][C:18](=[O:19])[C:17]2[CH:21]=[C:22]([C:25]([CH3:26])([CH3:27])[CH3:28])[C:23]([OH:24])=[C:15]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:16]=2)=[CH:3][CH:4]=1)([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 9784-Aminobenzoic AcidHCID 37871873,5-Di-tert-butyl-4-hydroxybenzoyl chloride

Product 1

HCID 164105R 8605Yield 32.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of 8.6g (0.063 mole) of p-aminobenzoic acid in 100 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 mixture was stirred at room temperature for 16 hours. The reaction mixture was then filtered. The filtrate was thereafter diluted with 200 ml of water and chilled. The resulting precipitate was collected, and was then recrystallized from a mixture of ethanol and water to give 3.6g of white needles of N-(4-carboxyphenyl)-3,5-di-t-butyl-4-hydroxybenzamide, m.p. 265°-266° C. Analysis: Calculated for C22H27NO4 : %C, 71.5; %H, 7.4; %N, 3.8; Found: %C, 71.7; %H, 7.3; %N, 3.6.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. additionThe filtrate was thereafter diluted with 200 ml of water
  3. temperaturechilled
  4. customThe resulting precipitate was collected
  5. customwas then recrystallized from a mixture of ethanol and water

Sources & evidence

ORD record
ord-df677b92cde04c3894471fab0b2d78bb
Source dataset
uspto-grants-1991_09
Patent number
US05049572

Reaction notes

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