HCID 69423728, compound → HCID 69421602, compound

HRID 1353063Notes

Reaction equation

HRID 1353063 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[C:5](=[CH:10][C:11]([O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH:17]=[CH:16]2)=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]>C1COCC1.[Pd]>[CH3:1][O:2][C:3](=[O:21])[C:4]1[C:5](=[CH:10][C:11]([O:14][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 1

HCID 69423728HCID 69423728, compound

Product 1

HCID 69421602HCID 69421602, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-(Cyclohex-2-enyloxy)-phthalic acid dimethyl ester [Example A37] (67 mg, 0.23 mmol) was hydrogenated under an atmosphere of hydrogen at room temperature and pressure with 10% wet Pd/C (ca. 200 mg) in THF (5 mL) for 24 h. The catalyst was removed by filtration and the solvent was evaporated under vacuum. The crude material was purified by flash chromatography on silica gel eluting with 0–20% MeOH in DCM to yield 4-cyclohexyloxy-phthalic acid dimethyl ester as an oil. m/z (APCI+) 293 (15%, [M+H]+), 179 (100), 261 (65).

Workup

  1. customwas hydrogenated under an atmosphere of hydrogen at room temperature
  2. customThe catalyst was removed by filtration
  3. customthe solvent was evaporated under vacuum
  4. customThe crude material was purified by flash chromatography on silica gel eluting with 0–20% MeOH in DCM

Sources & evidence

ORD record
ord-22c5ccee370b4ac98d247542d04019f1
Source dataset
uspto-grants-2007_05
Patent number
US07220777B2

Reaction notes

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