m-Chloroperbenzoic acid → 2,3-Epoxypropyl 6,7-epoxy-5,6,7,8-tetrahydro-1-naphthyl ether

HRID 1581072Notes

Reaction equation

HRID 1581072 reaction equation
[O:1]1[CH2:15][CH:2]1[CH2:3][O:4][C:5]1[C:14]2[CH2:13][CH:12]=[CH:11][CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.ClC1C=CC=C(C(OO)=[O:24])C=1>C(Cl)Cl>[O:24]1[CH:12]2[CH:11]1[CH2:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]([O:4][CH2:3][CH:2]3[O:1][CH2:15]3)[C:14]=1[CH2:13]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 110526861-(2,3-Epoxypropoxy)-5,8-dihydronaphthalene

Product 1

HCID 124457662,3-Epoxypropyl 6,7-epoxy-5,6,7,8-tetrahydro-1-naphthyl ether

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a well-stirred solution of 7 g. (0.03 m.) of 1-(2,3-epoxy-propoxy)-5,8-dihydro-naphthalene (prepared as described in application Ser. No. 768,176, filed Oct. 16, 1968, issued Oct. 13, 1970, as U.S. Pat. No. 3,534,085) in 60 ml. of CH2Cl2, 7.1 g. (0.03 m.) of 85% m-chloroperbenzoic acid in 100 ml. CH2Cl2 is added dropwise at such a rate that the temperature is maintained between 25° to 30° C. The mixture is stirred overnight at room temperature. The resulting precipitate (m-chlorobenzoic acid) is filtered off and the CH2Cl2 extract is washed successively with sat. NaHCO3 solution, and water. After drying (MgSO4), the solution is evaporated in vacuo to give 7.2 g. (95%) of oil which solidifies. A sample recrystallized from ether gives white needles, m.p. 85°-87°; λ Nujolmax 1330-1350 cm-1 (epoxy), τ CDCl3 absence of vinyl protons 4.0-4.2 region.

Workup

  1. temperatureis maintained between 25° to 30° C
  2. filtrationThe resulting precipitate (m-chlorobenzoic acid) is filtered off
  3. extractionthe CH2Cl2 extract
  4. washis washed successively with sat. NaHCO3 solution, and water
  5. dry with materialAfter drying (MgSO4)
  6. customthe solution is evaporated in vacuo
  7. customto give 7.2 g
  8. customA sample recrystallized from ether
  9. customgives white needles, m.p. 85°-87°

Sources & evidence

ORD record
ord-b7f31ff26b7a4157844d820b3400ddbd
Source dataset
uspto-grants-1976_01
Patent number
US03935267

Reaction notes

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