Water → HCID 178501163, compound

Dimethyl trans-cyclohexane-1,4-dicarboxylate (150.0 g) obtained in (1) above is dissolved in tetrahydrofuran (1500 ml), and to the solution is added dropwise a mixed solution of 28% sodium methoxide/methanol (149 g) and water (13.2 g) under ice-cooling. The reaction solution is warmed to room temperature, stirred for 3.5 hours, and thereto is poured n-hexane (1500 ml). The mixture is filtered to collect the precipitates. The resulting solid precipitates are added to a mixture of conc. hydrochloric acid (50 ml), water (450 ml) and chloroform (1000 ml) under ice-cooling, and the mixture is stirred at room temperature for 20 minutes. The chloroform layer is separated and the aqueous layer is extracted with chloroform. The organic layers are combined, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is crystallized from n-hexane, collected by filtration and dried to give trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (106.0 g). ESI-MS M/Z:185[M−H]−

1. temperaturecooling
2. filtrationThe mixture is filtered
3. customto collect the precipitates
4. customThe resulting solid precipitates
5. additionare added to a mixture of conc. hydrochloric acid (50 ml), water (450 ml) and chloroform (1000 ml) under ice-
6. temperaturecooling
7. stirringthe mixture is stirred at room temperature for 20 minutes
8. customThe chloroform layer is separated
9. extractionthe aqueous layer is extracted with chloroform
10. dry with materialdried over sodium sulfate
11. customevaporated
12. customto remove the solvent under reduced pressure
13. customThe resulting residue is crystallized from n-hexane
14. filtrationcollected by filtration
15. customdried

ORD record

ord-9dc8a7ace0f24104ac9f7e7eeb9de45a

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07605158B2