Hydrochloric Acid → 1,3-Bis(4-(3-hydroxy-4-nitrophenoxy)phenyl)adamantane

HRID 902587Notes

Reaction equation

HRID 902587 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]23[CH2:17][CH:12]4[CH2:13][CH:14]([CH2:16][C:10]([C:18]5[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=5)([CH2:11]4)[CH2:9]2)[CH2:15]3)=[CH:4][CH:3]=1.F[C:26]1[CH:27]=[CH:28][C:29]([N+:33]([O-:35])=[O:34])=[C:30]([OH:32])[CH:31]=1.[C:36]([O-:39])([O-])=O.[K+].[K+].Cl>O.CN(C=O)C>[OH:32][C:30]1[CH:31]=[C:26]([CH:27]=[CH:28][C:29]=1[N+:33]([O-:35])=[O:34])[O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]23[CH2:15][CH:14]4[CH2:13][CH:12]([CH2:11][C:10]([C:18]5[CH:19]=[CH:20][C:21]([O:24][C:26]6[CH:27]=[CH:28][C:29]([N+:33]([O-:35])=[O:34])=[C:36]([OH:39])[CH:31]=6)=[CH:22][CH:23]=5)([CH2:16]4)[CH2:9]2)[CH2:17]3)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium CarbonateHCID 44543464,4'-(1,3-Adamantanediyl)diphenol

Product 1

HCID 119527961,3-Bis(4-(3-hydroxy-4-nitrophenoxy)phenyl)adamantaneYield 93.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.00 g (6.26 mmol) of 1,3-bis(4-hydroxyphenyl)adamantane, 2.00 g (12.7 mmol) of 5-fluoro-2-nitrophenol, 1.70 g (12.3 mmol) of anhydrous K2CO3, and 50 mL of dry DMF was reflux for 12 h under nitrogen. The mixture was allowed to cool and subsequently poured into 500 mL of distilled water. The resulting solution was acidied by concentrated hydrogen chloride to PH=3.5˜4.0. The precipitated product was collected, washed thoroughly with water until neutral, and then dried to give 3.46 g (93.1%) of 1,3-bis(4-(3-hydroxy-4-nitrophenoxy)phenyl)adamantane. mp 118˜122° C.; Elemental Anal. Calcd. for C34H30N2O8: C, 68.69; H, 5.05; N, 4.71. Found: C, 68.56; H, 5.12; N, 4.65. MS (EI) m/z 594 (M+, 100); IR (KBr): 3416, 2890, 2857, 1556, 1342 cm−1.

Workup

  1. temperaturewas reflux for 12 h under nitrogen
  2. temperatureto cool
  3. customThe precipitated product was collected
  4. washwashed thoroughly with water until neutral, and
  5. customthen dried

Sources & evidence

ORD record
ord-d4b743c2985a443f8884c617a541e3f5
Source dataset
uspto-grants-2008_04
Patent number
US07365231B2

Reaction notes

Loading…