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) and the mixture is filtered to collect the precipitates. The resulting solid is 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).

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

ORD record

ord-4eb1984c18ea4c0482008f79d55b7f81

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07737161B2