Hydrochloric Acid → HCID 11953114, compound

HRID 902585Notes

Reaction equation

HRID 902585 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)[CH:15]3[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:17][CH:9]2[CH2:10]4)[CH2:14]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]2([C:18]3[CH:19]=[CH:20][C:21]([O:24][C:26]4[CH:27]=[CH:28][C:29]([N+:33]([O-:35])=[O:34])=[C:36]([OH:39])[CH:31]=4)=[CH:22][CH:23]=3)[CH:9]3[CH2:17][CH:13]4[CH2:12][CH:11]([CH2:16][CH:15]2[CH2:14]4)[CH2:10]3)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium CarbonateHCID 4332744-[2-(4-hydroxyphenyl)-2-adamantyl]phenol

Product 1

HCID 11953114HCID 11953114, compoundYield 73.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.00 g (6.26 mmol) of 2,2-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 2.75 g (73.9%) of 2,2-bis(4-(3-hydroxy-4-nitrophenoxy)phenyl)adamantane. mp 248˜250° C.; Elemental Anal. Calcd. for C34H30N2O8: C, 68.69; H, 5.05; N, 4.71. Found: C, 68.58; H, 5.10; N, 4.68. MS (EI) m/z 594 (M+, 100); IR (KBr): 3402, 2896, 2868, 1576, 1322 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-a81e4d6f2a614e348b52ffa70944eb4c
Source dataset
uspto-grants-2008_04
Patent number
US07365231B2

Reaction notes

Loading…