m-Chloroperbenzoic acid → HCID 58240633, compound

HRID 1802831Notes

Reaction equation

HRID 1802831 reaction equation
[C:1]([O:4][C:5]1[CH2:6][CH2:7][C:8]([CH3:19])([CH3:18])[C:9]23[CH2:15][CH:12]([CH2:13][CH2:14]2)[C:11]([CH3:17])([CH3:16])[C:10]=13)(=[O:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:28])C=1>C(Cl)Cl>[C:1]([O:4][C:5]12[CH:10]3[C:11]([CH3:17])([CH3:16])[CH:12]4[CH2:15][C:9]3([CH2:14][CH2:13]4)[C:8]([CH3:19])([CH3:18])[CH2:7][CH:6]1[O:28]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 58240635HCID 58240635, compound

Product 1

HCID 58240633HCID 58240633, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,2,7,7-tetramethyltricyclo[6.2.1.01.6]undecen-5-yl acetates described in Example 1a (2a+2b, 30.0 g, 95% pure, 0.11 mol) and MCPBA (36.5 g, 77% pure, 0.16 mol) in methylene chloride (300 ml) was stirred at room temperature (r. t.) for 24 h. An additional portion of MCPBA (10.0 g, 0.045 mol), added after 17 h, was necessary to complete the reaction. The reaction mixture was washed with aqueous sodium hydroxide solution and then water to pH 7 and negative peroxide test (KI paper), concentrated in vacuo and purified by flash chromatography (MTBE/hexane 1:9) to give a 61+37% mixture of 2,2,8,8-tetramethyl-5-oxatetracyclo[7.2.1.01.7.04.6]dodec-6-yl acetate (3) and the isomeric 2,2,8,8-tetramethyl-6-oxatetracyclo[7.2.1.01.7.05.7]dodec-5-yl acetate (14.8 g, 30+18% yield, pale yellow waxy solid). This mixture was used in the next steps without further purification.

Workup

  1. customthe reaction
  2. washThe reaction mixture was washed with aqueous sodium hydroxide solution
  3. concentrationwater to pH 7 and negative peroxide test (KI paper), concentrated in vacuo
  4. custompurified by flash chromatography (MTBE/hexane 1:9)

Sources & evidence

ORD record
ord-04055653d87f487abe3b01b2b5a89238
Source dataset
uspto-grants-2013_01
Patent number
US08349890B2

Reaction notes

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