m-Chloroperbenzoic acid → HCID 13575679, compound

HRID 465032Notes

Reaction equation

HRID 465032 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH2:12]([C:15]1[C:20]([Cl:21])=[C:19]([CH3:22])[CH:18]=[C:17]([N+:23]([O-:25])=[O:24])[C:16]=1[OH:26])[CH:13]=[CH2:14]>C(Cl)Cl>[Cl:21][C:20]1[C:15]2[CH2:12][CH:13]([CH2:14][OH:9])[O:26][C:16]=2[C:17]([N+:23]([O-:25])=[O:24])=[CH:18][C:19]=1[CH3:22]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 20261823HCID 20261823, compound

Product 1

HCID 13575679HCID 13575679, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

53 g of 85% MCPBA was added to a solution of 54 g of 7B in 500 ml of methylene chloride, and the mixture was stirred for 20 hours in the dark at room temperature, then filtered. The filtrate was washed with sodium bicarbonate solution, dried (MgSO4) and the solvent was evaporated. The residue was chromatographed over silica gel, using a 1:4:20 v:v:v mixture of tetrahydrofuran, ethyl acetate and hexane as eluent. The solid product that was obtained was recrystallized from ether to give 4-chloro-2,3-dihydro-2-(hydroxymethyl)-5-methyl-7-nitrobenzofuran (7C), as a light yellow solid, m.p.: 112°-115° C.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with sodium bicarbonate solution
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated
  5. customThe residue was chromatographed over silica gel
  6. additionv:v mixture of tetrahydrofuran, ethyl acetate and hexane as eluent
  7. customThe solid product that was obtained
  8. customwas recrystallized from ether

Sources & evidence

ORD record
ord-5aa1dc697e1b49fdb2da5ac8038b6196
Source dataset
uspto-grants-1985_10
Patent number
US04550121

Reaction notes

Loading…