Sodium Hydroxide → HCID 53781782, compound

HRID 361301Notes

Reaction equation

HRID 361301 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[CH:5][C:4]=1[C@@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[C:19]([O:21]CC)=[O:20].[OH-].[Na+]>C1COCC1.CO>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[CH:5][C:4]=1[C@@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[C:19]([OH:21])=[O:20]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53848261HCID 53848261, compound

Product 1

HCID 53781782HCID 53781782, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1.22 g (3.8 mmol) of trans-ethyl 2-(2,3,4-trimethoxyphenyl)cyclohexane-1-carboxylate in 20 mL of THF and 10 mL of methanol was added 10 mL of 10% aqueous NaOH. The mixture was stirred at room temperature for 18 h and heated at reflux for 18 h. After cooling, the bulk of the organic solvents was removed in vacuo and the residue was diluted with 100 mL of 5% aqueous NaOH and washed with 100 mL of ether. The aqueous layer was acidified to pH 1 with concentrated HCl and extracted with two 100 mL portions of ether. These ether extracts were combined, dried over MgSO4 and the solvent removed in vacuo to leave 0.88 g of trans-2-(2,3,4-trimethoxyphenyl)cyclohexane-1-carboxylic acid as an oil. 1H NMR (CDCl3) -- 1.3-2.2 (m, 8H), 2.65 (m, 1H), 3.1 (m, 1H), 3.8 (s, 9H), 6.6 (d, 1H), 6.8 (d, 1H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 18 h
  3. temperatureAfter cooling
  4. customthe bulk of the organic solvents was removed in vacuo
  5. additionthe residue was diluted with 100 mL of 5% aqueous NaOH
  6. washwashed with 100 mL of ether
  7. extractionextracted with two 100 mL portions of ether
  8. dry with materialdried over MgSO4
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-cc72c74eae394fe889ed340e4a1b9f07
Source dataset
uspto-grants-1999_02
Patent number
US05866513

Reaction notes

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