Hydrochloric Acid → 1-Methyl-4-[[2-(trimethylsilyl)ethoxy]methoxy]cyclohexane-1-carboxylic acid
Reaction equation
[CH3:1][C:2]1([C:17]([O:19]C)=[O:18])[CH2:7][CH2:6][CH:5]([O:8][CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH2:4][CH2:3]1.[OH-].[Na+].Cl>CO.O>[CH3:1][C:2]1([C:17]([OH:19])=[O:18])[CH2:3][CH2:4][CH:5]([O:8][CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:14])([CH3:15])[CH3:16])[CH2:6][CH2:7]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a 250-mL round-bottom flask containing a solution of methyl 1-methyl-4-[[2-(trimethylsilyl)ethoxy]methoxy]cyclohexane-1-carboxylate (3.6 g, 11.90 mmol, 1.00 equiv) in a mixed methanol/water (25 mL/4 mL) was added sodium hydroxide (2.38 g, 59.50 mmol, 5.00 equiv) and the resulting solution was heated to reflux overnight. After cooling, the pH value of the solution was adjusted to 4 with hydrochloric acid (2.0 M), extracted with 3×100 mL of ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The desired 1-methyl-4-[[2-(trimethylsilyl)ethoxy]methoxy]cyclohexane-1-carboxylic acid (3.12 g, 91%) was obtained as a light yellow oil which was used in the next step without further purification.
Workup
- temperaturethe resulting solution was heated
- temperatureto reflux overnight
- temperatureAfter cooling
- extractionextracted with 3×100 mL of ethyl acetate
- washThe combined organic layers were washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-e52d63ebf2794b5b86dfcba41ab1c5d6
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09212190B2
Reaction notes
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