Sulfuric Acid → HCID 18923794, compound

HRID 1379690Notes

Reaction equation

HRID 1379690 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=O)[CH:16]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[CH2:17][CH2:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:39]O.OS(O)(=O)=O.C([O-])(O)=O.[Na+]>C(O)CCC>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)=[CH:17][CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[N:39]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 18923796HCID 18923796, compound

Product 1

HCID 18923794HCID 18923794, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

The 1-(4-benzyloxyphenyl)-2,5-bis(4-methoxyphenyl)pentan-1,5-dione (9 g, 18 mmol), hydroxylamine hydrochloride (1.8 g, 26 mmol), and 0.8 mL concd H2SO4 were stirred in 250 mL of 1-butanol at 95°-100° C. for 18 h. The reaction mixture was neutralized with solid NaHCO3, worked up, purified, and recrystallised (EtOAC/ hexane) to give 3.2 g (37% yield) of white solid: mp 99°-102° C.; 1H NMR (CDCl3) d 3.82 (s, 3H, OCH3), 3.87 (s, 3H, OCH3), 5.06 (s, 2H, OCH2Ar), 6.83-6.89 (m, 4H, ArH), 6.99-7.02 (d, 2H, J=9, ArH), 7.14-7.17 (d, 2H, J=9, ArH), 7.32-7.45 (m, 7H, ArH), 7.64-7.71 (m, 2H, ArH), 8.08-8.11 (d, 2H, J=9, ArH); MS(FD) 473(M+). Anal. Calcd for C32H27NO3 : C, 81.16; H, 5.75; N, 2.96. Found: C, 81.10; H, 5.92; N, 2.98.

Workup

  1. custompurified
  2. customrecrystallised (EtOAC/ hexane)

Sources & evidence

ORD record
ord-7f5007e61d0a4c39a324cb25afa22459
Source dataset
uspto-grants-1997_09
Patent number
US05672609

Reaction notes

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