Water → HCID 21941826, compound
Reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]([O:16]C(C)(C)C)=[O:15].C1(C)C=CC(S(O)(=O)=O)=CC=1.O.[OH-].[Na+]>C(OCC)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To tert-butyl 2,5,8,11-tetraoxatetradecan-14-oate (65 g, 222.6 mmol) (example-1), was added p-toluenesulfonic acid (21.16 g, 111 mmol) and water (31.7 mL). The contents were heated to 80° C. and stirred at that temperature for 2 h. The completion of the reaction was monitor by TLC. The reaction mixture was cooled to 0° C. and basified to pH 10 to 11 using sodium hydroxide solution (17.7 g dissolved in 65 mL water). The contents were stirred at 25-30° C. for 10 minutes. Added Ethyl acetate (65 mL×2), stirred and separated the layer. The aqueous layer was cooled to 0 to 5° C. and the pH was adjusted to 3.5 to 4 using 11 N HCl solution and the product was extracted to methylene chloride (120 ml×2). The combined organic layer was washed with water, brine solution and dried over sodium sulphate. The solvent was removed under vacuum to afford 2,5,8,11-tetraoxatetradecan-14-oic acid (40.5 g, 77.1%).
Workup
- temperatureThe reaction mixture was cooled to 0° C. and basified to pH 10 to 11
- stirringThe contents were stirred at 25-30° C. for 10 minutes
- customseparated the layer
- temperatureThe aqueous layer was cooled to 0 to 5° C.
- extractionthe product was extracted to methylene chloride (120 ml×2)
- washThe combined organic layer was washed with water, brine solution
- dry with materialdried over sodium sulphate
- customThe solvent was removed under vacuum
Sources & evidence
- ORD record
- ord-de7773847bc447aea2bf56fa5f8a8e03
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040723B2
Reaction notes
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