Nitric Acid → 1-(Benzyloxy)-2,3-dimethoxybenzene

HRID 1977682Notes

Reaction equation

HRID 1977682 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N+]([O-])=O)[CH:12]=[C:11]([O:18][CH3:19])[C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C1C=CC=C(OC)C=1OC)(=O)C1C=CC=CC=1.[N+]([O-])(O)=O>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:18][CH3:19])[C:10]=1[O:20][CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 13270875(2,3-Dimethoxyphenyl)(phenyl)methanoneHCID 223268711-Benzyloxy-2,3-dimethoxy-5-nitrobenzene

Product 1

HCID 134470881-(Benzyloxy)-2,3-dimethoxybenzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The 1-benzyloxy-2,3-dimethoxy-5-nitrobenzene used as starting material was prepared by treating a solution of 1-benzoyl-2,3-dimethoxybenzene (7.25 g, 29.66 mmol) in glacial acetic acid (15 ml) portionwise with 70% nitric acid (2.84 ml) at room temperature. After 2 h, the reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic phase was washed with 1M NaOH, then brine, dried (MgSO4) and evaporated. The crude product was purified by column chromatography [silica 20% ethyl acetate-hexane] to give, after recrystallisation from CH2Cl2-hexane, the desired product (1.89 g) as a white solid m.p. 101-102°. MS m/z (relative intensity) (M+H)+289 [(M+H),+2%] 91[100%]. 1-Benzyloxy-2,3-dimethoxybenzene was prepared by the method of F Dietl et al Synthesis, 626 (1985).

Workup

  1. customwas prepared
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with 1M NaOH
  4. dry with materialbrine, dried (MgSO4)
  5. customevaporated
  6. customThe crude product was purified by column chromatography [silica 20% ethyl acetate-hexane]
  7. customto give
  8. customafter recrystallisation from CH2Cl2-hexane

Sources & evidence

ORD record
ord-211fa0de2f514bdf8d60232469a3fe0e
Source dataset
uspto-grants-2001_05
Patent number
US06235746B1

Reaction notes

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