Nitric Acid → HCID 66750548, compound

HRID 643917Notes

Reaction equation

HRID 643917 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH2:5]([CH:7]1[CH2:16][CH2:15][C:14]2[CH:13]=[C:12]([OH:17])[CH:11]=[CH:10][C:9]=2[CH2:8]1)[CH3:6]>CC(O)=O>[CH2:5]([CH:7]1[CH2:16][CH2:15][C:14]2[CH:13]=[C:12]([OH:17])[C:11]([N+:1]([O-:4])=[O:2])=[CH:10][C:9]=2[CH2:8]1)[CH3:6]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 450982142-Naphthalenol,6-ethyl-5,6,7,8-tetrahydro-(9CI)

Product 1

HCID 66750548HCID 66750548, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of HNO3 (65%, 1.05 mL, 23.0 mmol) in AcOH (10 mL) at 0° C. is added 6-ethyl-5,6,7,8-tetrahydronaphthalen-2-ol (2.02 g, 11.5 mmol) in AcOH (33 mL) dropwise. It is allowed to warm to ambient temperature and stirred for 1.5 h and then at 40° C. until starting material is completely consumed. Water is added, followed by EtOAc. The organic layer is concentrated and purified by column chromatography to give the title compound as a yellow oil: 1H NMR (CDCl3) δ 0.91 (t, J=7 Hz, 3H), 1.28-1.36 (m, 3H), 1.51-1.56 (m, 1H), 1.85-1.90 (m, 1H), 2.24-2.31 (m, 1H), 2.72-2.64 (m, 3H), 6.77 (s, 1H), 7.73 (s, 1H), 10.29 (s, 1H).

Workup

  1. customat 40° C.
  2. customis completely consumed
  3. additionWater is added
  4. concentrationThe organic layer is concentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-4d35c0fa2a26409eb50581595386e107
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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