HCID 20745894, compound → HCID 20745895, compound

HRID 2308132Notes

Reaction equation

HRID 2308132 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][Cl:21])[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.[H][H]>C(OCC)(=O)C.CCCCCC.C(OCC)(=O)C>[CH3:10][O:9][C:7]([CH:6]1[CH2:11][CH:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][Cl:21])[CH2:13][CH:4]([C:3]([O:2][CH3:1])=[O:22])[CH2:5]1)=[O:8]

Participants

5

Reactant 2

HCID 20745894HCID 20745894, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 20745895HCID 20745895, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

7.5 g (22.8 mmol) 5-[(6-chlorohexyl)oxy]isophthalic acid dimethyl ester (example 6) were dissolved in 75 ml ethyl acetate and charged into a steel autoclave. After addition of 3 g of a hydrogenation catalyst (5% Rh/Alox, Johnson Matthey Company) the vessel was closed and the compound was hydrogenated at a reaction temperature of 70° C. using a constant hydrogen pressure of 18 bar until no further hydrogen uptage was observed (approx. 4 hours). The reaction suspension was cooled to room temperature, filtered and concentrated under vacuum to dryness. The crude product was essentially a cis/trans mixture of 5-[(6-chlorohexyl)oxy]-1,3-cyclohexanedicarboxylic acid dimethyl ester. The pure cis-compound was isolated as a colourless oil by chromatography on silica gel using hexane/ethyl acetate (4:1) as eluent. (yield: 6.1 g, 80%).

Workup

  1. customwas closed
  2. customwas hydrogenated at a reaction temperature of 70° C.
  3. custom(approx. 4 hours)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum to dryness
  6. additiona cis/trans mixture of 5-[(6-chlorohexyl)oxy]-1,3-cyclohexanedicarboxylic acid dimethyl ester
  7. customThe pure cis-compound was isolated as a colourless oil by chromatography on silica gel

Sources & evidence

ORD record
ord-a121da962c744537bb64ee6dd92483a1
Source dataset
uspto-grants-2004_12
Patent number
US06833421B1

Reaction notes

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