Acetic Acid → HCID 67300448, compound

HRID 1015529Notes

Reaction equation

HRID 1015529 reaction equation
[OH-].[Na+].BrBr.Br[O-].[CH2:7]([O:14][C:15]12[CH2:23][CH:19]3[CH2:20][CH:21]([CH2:22]1)[C:17]([C:24](=[O:26])C)([CH2:18]3)[CH2:16]2)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CC(C)=[O:29].CC(O)=O>O1CCOCC1.O>[CH2:7]([O:14][C:15]12[CH2:23][CH:19]3[CH2:20][CH:21]([CH2:22]1)[C:17]([C:24]([OH:29])=[O:26])([CH2:18]3)[CH2:16]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 67300417HCID 67300417, compound

Product 1

HCID 67300448HCID 67300448, compoundYield 83.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

To a mixture of NaOH (10.8 g, 270 mmol), H2O (72 mL) and 1,4-dioxane (20 mL) at ice bath temperature was added Br2 (5.2 mL, 100.8 mmol) and stirred for 5 minutes. This hypobromite solution was added drop-wise to a solution of the compound obtained from step III (4.84 g, 18 mmol) in 1,4-dioxane (18 mL) kept at ice bath temperature. The reaction mixture was gradually warmed to room temperature and stirred for 1 h, after which it was cooled to ice bath temperature and quenched by adding AcOH (3.9 mL, 65.7 mmol), diluted with water, and extracted in EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and the solvent was removed under reduced pressure to obtain 1-(benzyloxy)tricyclo[3.3.1.03,7]nonane-3-carboxylic acid as a gummy liquid (4.1 g) in 83% yield. m/z (M+1), 273; 1H NMR (CDCl3) 300 MHz δ 7.40-7.20 (m, 5H), 4.52 (s, 2H), 2.78-2.70 (m, 1H), 2.58-2.48 (m, 1H), 2.45-2.37 (m, 1H), 2.18-1.50 (m, 9H).

Workup

  1. customkept at ice bath
  2. stirringstirred for 1 h
  3. temperatureafter which it was cooled to ice bath temperature
  4. customquenched
  5. extractionextracted in EtOAc
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-855a0c95bbf24584943d4950786d647d
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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