m-Chloroperbenzoic acid → HCID 90408609, compound

HRID 1855062Notes

Reaction equation

HRID 1855062 reaction equation
[CH2:1]=[C:2]1[CH2:7][CH2:6][C:5]([CH2:21][OH:22])([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:9]=2)[CH2:4][CH2:3]1.ClC1C=CC=C(C(OO)=[O:31])C=1>C(Cl)Cl.CCOC(C)=O>[O:14]([C:10]1[CH:9]=[C:8]([C:5]2([CH2:21][OH:22])[CH2:4][CH2:3][C:2]3([O:31][CH2:1]3)[CH2:7][CH2:6]2)[CH:13]=[CH:12][CH:11]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 90408594HCID 90408594, compound

Product 1

HCID 90408609HCID 90408609, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4-methylene-1-(3-phenoxyphenyl)cyclohexyl)methanol (53 mg, 0.180 mmol) in CH2Cl2 (0.9 mL) at 0° C. was added m-chloroperbenzoic acid (43.5 mg, 0.252 mmol). The solution was warmed to rt and stirred for 1 h. The reaction mixture was diluted with EtOAc, washed successively with 1 N aqueous NaOH, water, and brine, dried (MgSO4), filtered, and concentrated in vacuo to afford the title compound (56 mg, 100% yield) as a colorless oil. LCMS, [M+H]+=311.1.

Workup

  1. washwashed successively with 1 N aqueous NaOH, water, and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-427cc09bc6b749ba9a4d8e24991cb7bc
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

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