Acetic Acid → Dimethyl 5-hydroxycyclohexane-1,3-dicarboxylate

HRID 2199449Notes

Reaction equation

HRID 2199449 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[C:12]([OH:14])[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.C(O)(=O)C>CO.[Rh]>[CH3:10][O:9][C:7]([CH:6]1[CH2:11][CH:12]([OH:14])[CH2:13][CH:4]([C:3]([O:2][CH3:1])=[O:15])[CH2:5]1)=[O:8]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester

Product 1

HCID 58237130Dimethyl 5-hydroxycyclohexane-1,3-dicarboxylateYield 83.6%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of dimethyl-5-hydroxyisophthalate (3.50 g, 16.6 mmol) in methanol (60.0 mL) was added 5% rhodium on alumina (0.80 g) at 0° C., followed by acetic acid (0.60 mL, 10.6 mmol). The reaction mixture was shaken under hydrogen (55 psi) at room temperature overnight and then filtered through Celite® and concentrated under reduced pressure. The residue was purified by CombiFlash® system (12 g silica gel cartridge; gradient: 0 to 50% ethyl acetate in DCM over 30 min) to give 3.00 g (83%) of the title compound, 5-hydroxy-cyclohexane-1,3-dicarboxylic acid dimethyl ester. 1H NMR (400 MHz, CDCl3): δ 3.56-3.78 (m, 7H), 2.15-2.51 (m, 5H), 1.25-1.66 (m, 3H).

Workup

  1. filtrationfiltered through Celite®
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by CombiFlash® system (12 g silica gel cartridge; gradient: 0 to 50% ethyl acetate in DCM over 30 min)

Sources & evidence

ORD record
ord-074e5e8fb3f94986b97ad4fa609b3706
Source dataset
uspto-grants-2016_06
Patent number
US09359297B2

Reaction notes

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