Sodium Hydroxide → HCID 68602662, compound

HRID 2363901Notes

Reaction equation

HRID 2363901 reaction equation
C([C@@:3]1([C:22]([OH:24])=[O:23])[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[O:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)C.[OH-].[Na+]>CCO>[CH3:21][O:20][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[O:18][CH3:19])[CH2:11][CH2:10][O:9][C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:3]1[C:22]([OH:24])=[O:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86642594ethyl (1R,2R)-2-(3,4-dimethoxyphenethoxy)cyclohexane-1-carboxylic acid

Product 1

HCID 68602662HCID 68602662, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of crude (1R,2R)-2-(3,4-dimethoxyphenethoxy)cyclohexane-1-carboxylic acid (167) (3.71 g, 10 mmol) and 4M NaOH aq (10 mL, 40 mmol) in EtOH (25 mL) was stirred at room temperature for 18 hrs. The reaction mixture was then concentrated in vacuo, the residue was re-dissolved in water (25 mL) and the resultant basic aqueous solution was extracted with diethyl ether (2×25 mL). The aqueous layer was collected, acidified to pH1 with 6M HCl aq and extracted with dichloromethane (2×25 mL). The combined organic extracts were dried over anhydrous MgSO4 and concentrated in vacuo to give 2.29 g of (1R,2R)-2-(3,4-dimethoxyphenethoxy)cyclohexane-1-carboxylic acid (168) (74% yield; Rt: 13.48 min (HPLC-method A); 1H-NMR (300 MHz, CDCl3) δ: 7.95 (br s, 1H, CO2H), 6.78-6.69 (m, 3H, Ar), 3.84 (s, 3H, CH3O), 3.82 (s, 3H, CH3O), 3.81 (overlapped dt, J 14 Hz & 7 Hz, 1H, CH2aO), 3.57 (dt, J 14 Hz & 7 Hz, 1H, CH2bO), 3.52-3.42 (m, 1H, CHO), 2.79 (t, J 7 Hz, 2H, CH2), 2.34 (dt, J 14 Hz & 6 Hz, 1H, CHN), 2.13-1.09 (m, 8H, Aliph); MS (ES+) 307.1 [M+H]+.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. dissolutionthe residue was re-dissolved in water (25 mL)
  3. extractionthe resultant basic aqueous solution was extracted with diethyl ether (2×25 mL)
  4. customThe aqueous layer was collected
  5. extractionextracted with dichloromethane (2×25 mL)
  6. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-21e310141bcb444cae5f467b2ca449aa
Source dataset
uspto-grants-2014_04
Patent number
US08692002B2

Reaction notes

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