Hydrochloric Acid → HCID 15599094, compound

HRID 986801Notes

Reaction equation

HRID 986801 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]=1[OH:21])[NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=[O:13])([CH3:4])([CH3:3])[CH3:2].[C:26]1(=[O:32])[O:31][C:29](=[O:30])[CH2:28][CH2:27]1.Cl.C(O)(=O)CCC(O)=O>N1C=CC=CC=1.O>[C:12]([C:11]1[CH:10]=[C:9]([N:8]([C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:20]([OH:21])=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:18]=2)[C:26](=[O:32])[CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH:17]=[CH:16][CH:15]=1)([OH:14])=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1110Succinic AcidHCID 7922Succinic anhydrideHCID 601943-(3,5-DI-T-Butyl-4-hydroxyanilino)benzoic acid

Product 1

HCID 15599094HCID 15599094, compoundYield 47.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1049PyridineSolvent

Conditions

Temperature
150 °C

Procedure

Under a nitrogen atmosphere, a mixture of 3.0 g (0.0088 mole) of 3-(3,5-di-t-butyl-4-hydroxyanilino)benzoic acid and 9.0 g (0.090 mole) of succinic anhydride was heated at 150° C. for 15 minutes. The reaction mixture was diluted with pyridine (50 ml) and water, and was poured into cold dilute hydrochloric acid. The resulting precipitate was recrystallized from a mixture of 14 ml of ethanol and 22 ml of water to give a white solid. This solid was heated in 70 ml of water to dissolve any succinic acid, and was collected and heated in 40 ml of ethyl acetate. The ethyl acetate solution was filtered to remove a small amount of insoluble material. The ethyl acetate filtrate was concentrated to 20 ml, and was then diluted with 10 ml of hexane. The resulting precipitate was collected and dried to give 1.85 g of white solid N-(3-carboxyphenyl)-N-(3,5-di-t-butyl-4-hydroxyphenyl)succinamic acid, m.p. 182°-183° C. Analysis: Calculated for C25H31NO6 : % C, 68.0; % H, 7.1; % N, 3.2; Found: % C, 68.2; % H, 7.1; % N, 3.0.

Workup

  1. customThe resulting precipitate was recrystallized from a mixture of 14 ml of ethanol and 22 ml of water
  2. customto give a white solid
  3. customwas collected
  4. temperatureheated in 40 ml of ethyl acetate
  5. filtrationThe ethyl acetate solution was filtered
  6. customto remove a small amount of insoluble material
  7. concentrationThe ethyl acetate filtrate was concentrated to 20 ml
  8. additionwas then diluted with 10 ml of hexane
  9. customThe resulting precipitate was collected
  10. customdried

Sources & evidence

ORD record
ord-110e6d3c0c724241950484e6f38f50ed
Source dataset
uspto-grants-1987_12
Patent number
US04716178

Reaction notes

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