Hydrochloric Acid → 1-(4-Nitrophenyl)tricyclo[3.3.1.03,7]nonane-3-carboxylic acid

HRID 1015516Notes

Reaction equation

HRID 1015516 reaction equation
[OH-:1].[Na+].BrBr.Br[O-].[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]23[CH2:24][CH:20]4[CH2:21][CH:22]([CH2:23]2)[C:18]([C:25](=[O:27])C)([CH2:19]4)[CH2:17]3)=[CH:12][CH:11]=1)([O-:9])=[O:8].Cl>O1CCOCC1.O>[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]23[CH2:24][CH:20]4[CH2:21][CH:22]([CH2:23]2)[C:18]([C:25]([OH:1])=[O:27])([CH2:19]4)[CH2:17]3)=[CH:12][CH:11]=1)([O-:9])=[O:8]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24408BromineHCID 5460626HypobromiteHCID 670178651-[1-(4-Nitrophenyl)tricyclo[3.3.1.03,7]non-3-yl]ethanone

Product 1

HCID 670178551-(4-Nitrophenyl)tricyclo[3.3.1.03,7]nonane-3-carboxylic acidYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of NaOH (6.3 g, 158.0 mmol), H2O (54.0 mL) and 1,4 dioxane (7 mL) at ice bath temperature was added Br2 (3.2 mL, 59.0 mmol) and stirred for 5 minutes. The formed hypobromite solution was added dropwise to a stirred solution of 1-[1-(4-nitrophenyl)tricyclo[3.3.1.03,7]non-3-yl]ethanone (3.0 g, 10.53 mmol) obtained in step I, in 1,4-dioxane (14 mL) at ice bath temperature. The reaction mixture was gradually warmed to r.t. and after 1 h, it was cooled to ice bath temperature and acidified with conc. HCl, diluted with water, and extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and the solvent was removed under reduced pressure to obtain 1-(4-nitrophenyl)tricyclo[3.3.1.03,7]nonane-3-carboxylic acid (2.27 g) in 75% yield as off-white solid; M.R: 145-150° C. m/z (M−1) 286; IR cm−1 3437, 2945, 1693, 1596, 1511, 1408, 1352, 946, 839, 749. 1H NMR (CDCl3) 300 MHz δ 8.16 (d, J=8.8 Hz, 2H), 7.42 (d, J=8.8 Hz, 2H), 2.96-2.88 (m, 1H), 2.59-2.52 (m, 1H), 2.44-2.33 (m, 1H), 2.23-2.03 (m, 4H), 2.02-1.68 (m, 5H).

Workup

  1. temperatureit was cooled to ice bath temperature
  2. extractionextracted with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1f3698823a8f469093994e8b6d7e8c2e
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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