Nitric Acid → 1-(5-(Benzyloxy)-2-hydroxy-3-nitrophenyl)ethanone

HRID 1967185Notes

Reaction equation

HRID 1967185 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[C:16](=[O:18])[CH3:17].[N+:19]([O-])([OH:21])=[O:20]>C(O)(=O)C>[OH:1][C:2]1[C:7]([N+:19]([O-:21])=[O:20])=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[C:16](=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 128709281-[5-(Benzyloxy)-2-hydroxyphenyl]ethan-1-one

Product 1

HCID 210728231-(5-(Benzyloxy)-2-hydroxy-3-nitrophenyl)ethanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

10.00 kg (41.27 mol) 1-[2-hydroxy-5-(phenylmethoxy)-phenyl]-ethanone 5a are dissolved in 50 l acetic acid. 4.40 kg (45.40 mol) nitric acid 65% are metered into this solution at 15 to 20° C. The feed vessel is rinsed with 4 l acetic acid. The reaction mixture is stirred for 1 hour. After inoculation 50 l water are added. The suspension obtained is stirred for 1 hour at 10° C. to complete the crystallisation. The product is centrifuged and dried at 50° C.

Workup

  1. customare metered into this solution at 15 to 20° C
  2. washThe feed vessel is rinsed with 4 l acetic acid
  3. additionAfter inoculation 50 l water are added
  4. customThe suspension obtained
  5. stirringis stirred for 1 hour at 10° C.
  6. customthe crystallisation
  7. customdried at 50° C.

Sources & evidence

ORD record
ord-8975e70275e24129a376e4cca65a41f4
Source dataset
uspto-grants-2013_04
Patent number
US08420809B2

Reaction notes

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