m-Chloroperbenzoic acid → HCID 11447722, compound

HRID 1867220Notes

Reaction equation

HRID 1867220 reaction equation
[CH3:1][CH:2]1[C:6]2([CH2:11][CH:10]([CH3:12])[CH2:9][C:8]([CH3:14])([CH3:13])[CH2:7]2)[C:5](=[CH2:15])[C:4](=[O:16])[CH2:3]1.ClC1C=CC=C(C(OO)=[O:25])C=1>C(Cl)Cl>[CH3:13][C:8]1([CH3:14])[CH2:9][CH:10]([CH3:12])[CH2:11][C:6]2([CH:2]([CH3:1])[CH2:3][C:4](=[O:16])[C:5]32[O:25][CH2:15]3)[CH2:7]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 69027320HCID 69027320, compound

Product 1

HCID 11447722HCID 11447722, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

At 0° C., a solution of 4,7,7,9-tetramethyl-1-methylenespiro[4.5]decan-2-one (1.43 g, 6.49 mmol), in CH2Cl2 (10 mL) was added dropwise within 45 min. to a stirred solution of 70% 3-chloroperbenzoic acid (1.76 g, 7.14 mmol) in CH2Cl2 (20 mL). After further stirring at 0° C. for 1 h, the cooling bath was removed, and the reaction mixture stirred for 3 d, with an additional portion of 70% 3-chloroperbenzoic acid (1.76 g, 7.14 mmol) being added after the first and second day. The insoluble material was removed by vacuum filtration and washed with CH2Cl2. The combined organic solutions were washed with 20% aq. NaHSO3, halfconc. NaHCO3, and water (50 mL), the aqueous washings again extracted with CH2Cl2 (50 mL). The combined organic extracts were dried (Na2SO4) and concentrated in a rotary evaporator. The resulting residue was purified by silica-gel FC (pentane/Et2O, 19:1, Rf=0.11) to provide 6,6,8,10-tetramethyl-1-oxadispiro[2.0.5.3]dodecan-12-one (930 mg, 61%).

Workup

  1. customthe cooling bath was removed
  2. additionbeing added after the first and second day
  3. customThe insoluble material was removed by vacuum filtration
  4. washwashed with CH2Cl2
  5. washThe combined organic solutions were washed with 20% aq. NaHSO3, halfconc
  6. extractionNaHCO3, and water (50 mL), the aqueous washings again extracted with CH2Cl2 (50 mL)
  7. dry with materialThe combined organic extracts were dried (Na2SO4)
  8. concentrationconcentrated in a rotary evaporator
  9. customThe resulting residue was purified by silica-gel FC (pentane/Et2O, 19:1, Rf=0.11)

Sources & evidence

ORD record
ord-1b030075f6124d66b34c22c8e627ce18
Source dataset
uspto-grants-2009_12
Patent number
US07632791B2

Reaction notes

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