Sodium Hydroxide → HCID 69469447, compound

HRID 1296222Notes

Reaction equation

HRID 1296222 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1([C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17]C)=[O:16])[OH:11])[CH3:3].[OH-].[Na+]>CO>[CH3:3][N:2]([CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1([C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([OH:17])=[O:16])[OH:11])[CH3:1]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69469906HCID 69469906, compound

Product 1

HCID 69469447HCID 69469447, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A sample of methyl 3-[(1-RS,2-RS)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-benzoate (2.5 g, 8.6 mmol), MeOH (20 mL), and 3N NaOH (9 mL) were refluxed for 1.5 h. The MeOH was evaporated in vacuo and the residue was made acidic with HCl (conc). The solvent was evaporated in vacuo and the residue triturated with Et2O. The solid was dried overnight in vacuo to give 2.2 g (92%) 3-[(1-RS,2-RS)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-benzoic acid.

Workup

  1. customThe MeOH was evaporated in vacuo
  2. customThe solvent was evaporated in vacuo
  3. customthe residue triturated with Et2O
  4. customThe solid was dried overnight in vacuo

Sources & evidence

ORD record
ord-3066d0818ef2497685632501e66c5759
Source dataset
uspto-grants-2007_07
Patent number
US07244866B2

Reaction notes

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