Dichloromethane → HCID 15598815, compound

HRID 1085387Notes

Reaction equation

HRID 1085387 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:12]([OH:19])=[C:11]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:10]=2)=[CH:5][CH:4]=1.[O:24]1[CH2:30][C:29](=[O:31])[O:28][C:26](=[O:27])[CH2:25]1.C(N(CC)CC)C.ClCCl>C(COC)OC.C(O)C.O>[C:20]([C:11]1[CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([NH:2][C:29](=[O:31])[CH2:30][O:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:4][CH:5]=2)[CH:14]=[C:13]([C:15]([CH3:16])([CH3:17])[CH3:18])[C:12]=1[OH:19])([CH3:23])([CH3:22])[CH3:21]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 782321,4-Dioxane-2,6-dioneHCID 20059577HCID 20059577, compound

Product 1

HCID 15598815HCID 15598815, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 16.7 g (0.050 mole) of 4'-amino-3,-5-di-tertiary-butyl-4-hydroxybiphenyl hydrochloride and 7.0 g (0.060 mole) of oxydiacetic anhydride in 200 ml of glyme was added 0.050 mole of triethylamine and the solution was warmed at 70° C. for one hour. The solution was cooled and a 50:50 mixture of dichloromethane and water was added. The organic layer was separated, washed with water twice and dried over magnesium sulfate. Filtration and evaporation provided a residue which was triturated with hexane and chilled. The solid was separated by filtration. Recrystallization from a mixture of chloroform and hexane gave a grey solid. The solid was dissolved in 23 ml of ethanol, the solution was filtered and 10 ml of water was added to the filtrate. The filtrate was cooled and the resulting precipitate was separated by filtration and dried to provide N-(3',5'-di-tertiary-butyl-4'-hydroxy-4-biphenylyl)diglycolamic acid, m.p. 183°-184° C. Analysis: Calculated for C24H31NO5 : % C, 69.7; % H, 7.5; % N, 3.4; Found: % C, 69.9; % H, 7.6; % N, 3.1.

Workup

  1. temperatureThe solution was cooled
  2. additionwas added
  3. customThe organic layer was separated
  4. washwashed with water twice
  5. dry with materialdried over magnesium sulfate
  6. filtrationFiltration and evaporation
  7. customprovided a residue which
  8. customwas triturated with hexane
  9. temperaturechilled
  10. customThe solid was separated by filtration
  11. customRecrystallization
  12. additionfrom a mixture of chloroform and hexane
  13. customgave a grey solid
  14. filtrationthe solution was filtered
  15. addition10 ml of water was added to the filtrate
  16. temperatureThe filtrate was cooled
  17. customthe resulting precipitate was separated by filtration
  18. customdried

Sources & evidence

ORD record
ord-094c954c42c4423f86ee39e8ddd79bf3
Source dataset
uspto-grants-1991_04
Patent number
USRE033574

Reaction notes

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