2-Aminophenol → HCID 19878523, compound

HRID 1885952Notes

Reaction equation

HRID 1885952 reaction equation
[P:1](Cl)(Cl)[O:2][C:3]1[C:8]([C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:7][C:6]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:16])=[CH:5][C:4]=1[C:36]([CH3:39])([CH3:38])[CH3:37].C(=O)=O.CC(C)=O.[NH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=1[OH:56].C(N(CC)CC)C>C(Cl)Cl>[C:36]([C:4]1[CH:5]=[C:6]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:16])[CH:7]=[C:8]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:3]=1[O:2][P:1]1[NH:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=2[O:56]1)([CH3:39])([CH3:38])[CH3:37]

Participants

6

Reactant 4

HCID 58012-AminophenolHCID 8471TriethylamineHCID 18522661Acetone cardiceHCID 19742195HCID 19742195, compound

Product 1

HCID 19878523HCID 19878523, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a cooled solution of 29.8 g (50 mmol) of 2,6-di-tert-butyl-4-[2-(n-octadecyloxycarbonyl)ethyl]-phenyl phosphorodichloridite in 100 ml of methylene chloride at dry ice/acetone temperature is added a solution of 5.46 g (50 mmol) of 2-aminophenol and 13.95 ml (100 mmol) of triethylamine in 25 ml of methylene chloride. After the addition is complete, the mixture is warmed to room temperature with continual stirring. After 16 hours, the reaction mixture is concentrated under reduced pressure, mixed with 50 ml of toluene and filtered to remove insoluble solids. The filtrate is reconcentrated, dissolved in hexane and treated with decolorizing charcoal. The resultant mixture is clarified and the filtrate concentrated under reduced pressure to give 27.6 g of the title compound as a white solid melting at 58°-65° C.

Workup

  1. additionAfter the addition
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. additionmixed with 50 ml of toluene
  4. filtrationfiltered
  5. customto remove insoluble solids
  6. dissolutiondissolved in hexane
  7. additiontreated with decolorizing charcoal
  8. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-4613862d93924d0c860a261f9cb0d1cc
Source dataset
uspto-grants-1992_09
Patent number
US05147909

Reaction notes

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