m-Chloroperbenzoic acid → 6-nitro-2,2,3-trimethyl-3,4-dihydro-3,4-epoxy-2H-1-benzopyran

HRID 1655374Notes

Reaction equation

HRID 1655374 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:15])=[CH:9][C:8]=2[CH:16]=1)([O-:3])=[O:2].ClC1C=CC=C(C(OO)=[O:25])C=1>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:13])([CH3:14])[C:10]3([CH3:15])[O:25][CH:9]3[C:8]=2[CH:16]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 157118816-nitro-2,2,3-trimethyl-2H-1-benzopyran

Product 1

HCID 157118886-nitro-2,2,3-trimethyl-3,4-dihydro-3,4-epoxy-2H-1-benzopyranYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-nitro-2,2,3-trimethyl-2H-1-benzopyran (10.0 g, 0.0457 mol) in dichloromethane (200 ml) at 0° C. was added m-chloroperbenzoic acid (13.5 g, 70%, 0.0548 mol). After stirring for eighteen hours at room temperature the mixture was washed successively with water, aqueous sodium hydrogen carbonate, water and then aqueous sodium hydroxide solution. The organic phase was separated and evaporated under reduced pressure to give 9.96 g (93%) of 6-nitro-2,2,3-trimethyl-3,4-dihydro-3,4-epoxy-2H-1-benzopyran, 1H NMR (CDCl3): δ 1.3 (s, 3H) , 1.55 (s, 3H) , 1.60 (s,3H), 3.8 (s,1H), 6.9 (d,1H), 8.15 (d,1H), 8.30 (s,1H).

Workup

  1. washwas washed successively with water, aqueous sodium hydrogen carbonate, water
  2. customThe organic phase was separated
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-639111dcc036473abd594f639304cc16
Source dataset
uspto-grants-1993_10
Patent number
US05250547

Reaction notes

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