Acetic Acid → HCID 67017835, compound

HRID 1015511Notes

Reaction equation

HRID 1015511 reaction equation
[OH-].[Na+].BrBr.Br[O-].[CH2:7]([O:14][CH2:15][C:16]12[CH2:24][CH:20]3[CH2:21][CH:22]([CH2:23]1)[C:18]([C:25](=[O:27])C)([CH2:19]3)[CH2:17]2)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CC(O)=[O:30]>O1CCOCC1.O>[CH2:7]([O:14][CH2:15][C:16]12[CH2:24][CH:20]3[CH2:21][CH:22]([CH2:23]1)[C:18]([C:25]([OH:30])=[O:27])([CH2:19]3)[CH2:17]2)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 24408BromineHCID 5460626HypobromiteHCID 67300444HCID 67300444, compound

Product 1

HCID 67017835HCID 67017835, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

To a mixture of NaOH (30.6 g, 765 mmol), H2O (255 mL) and 1,4 dioxane (51 mL) at ice bath temperature was added Br2 (15.2 mL, 285.6 mmol) and stirred for 15 minutes. This hypobromite solution was added dropwise to a stirred solution of 1-{1-[(benzyloxy)methyl]tricyclo[3.3.1.03,7]non-3-yl}ethanone (14.5 g, 51.0 mmol) in 1,4-dioxane (51 mL) at ice bath temperature. The reaction mixture was gradually warmed to r.t. and stirred for 1 h. The reaction mixture was cooled to ice bath temperature and quenched by adding AcOH (46.7 mL, 765 mmol). The reaction mixture was diluted with water, extracted with EtOAc, the combined organic layers were washed with brine, dried over Na2SO4, and the solvent was removed under reduced pressure to obtain 1-[(benzyloxy)methyl]tricyclo[3.3.1.03,7]nonane-3-carboxylic acid (8.0 g) as white solid in 55% yield. m/z (M−1), 285; 1H NMR (CDCl3) 300 MHz δ 7.40-7.22 (m, 5H), 4.50 (s, 2H), 3.27 (s, 2H), 2.70-2.62 (m, 1H), 3.47-3.38 (m, 1H), 2.16 (s, 2H), 2.12-1.98 (m, 2H), 1.90-1.55 (m, 7H), 1.50 (dd, J=3.0, 11.0 Hz, 1H).

Workup

  1. stirringstirred for 1 h
  2. temperatureThe reaction mixture was cooled to ice bath temperature
  3. customquenched
  4. extractionextracted with EtOAc
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-aefbc05efbe0476782b14463c9675fae
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

Loading…