Acetic Anhydride → acetic acid (1RS,3RS,4RS)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexyl ester

HRID 1867473Notes

Reaction equation

HRID 1867473 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH:16]([N+:17]([O-:19])=[O:18])[CH2:15][CH2:14][CH:13]([OH:20])[CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:21](OC(=O)C)(=[O:23])[CH3:22]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH:16]([N+:17]([O-:19])=[O:18])[CH2:15][CH2:14][CH:13]([O:20][C:21](=[O:23])[CH3:22])[CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 17989075(1RS,3RS,4RS)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexanol2×

Product 1

HCID 67022378acetic acid (1RS,3RS,4RS)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexyl ester

Conditions

Temperature
100 °C

Procedure

6.0 g of (±)-(1SR,3RS,4SR)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexanol (compound E5) are dissolved in 40 ml of acetic anhydride and stirred for 1.5 h at 100° C. The reaction mixture is concentrated and the residual title compound of melting point 108-110° C. is used without further purification in the next step.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe residual title compound of melting point 108-110° C. is used without further purification in the next step

Sources & evidence

ORD record
ord-84be4edf620d450ea4f67728584961ff
Source dataset
uspto-grants-2009_12
Patent number
US07632844B2

Reaction notes

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