1,4-Dioxane → HCID 19068275, compound

HRID 1957699Notes

Reaction equation

HRID 1957699 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([CH:24]=[CH:25][C:26]=3[O:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:14]([O:16]CC3C=CC=CC=3)=[O:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.O1CCOCC1>[Pd].C(O)(=O)C>[C:1]12([C:11]3[CH:12]=[C:13]([CH:24]=[CH:25][C:26]=3[O:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:14]([OH:16])=[O:15])[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 19068293HCID 19068293, compound

Product 1

HCID 19068275HCID 19068275, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

2.34 g (5.38 mmol) of benzyl 3-(1-adamantyl)-4-methoxycarbonylmethyloxybenzoate, 40 ml of dioxane, 500 μl of acetic acid and 234 mg of palladium (10%) were introduced into a reactor. The mixture was hydrogenated at 40° C. and at a pressure of 7 bar for three hours. The catalyst was filtered off and the mixture was evaporated to dryness. The solid obtained was triturated from hexane, filtered off and dried. 1.74 g (94%) of the expected acid, having a melting point of 230°-1° C., was recovered.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe mixture was evaporated to dryness
  3. customThe solid obtained
  4. customwas triturated from hexane
  5. filtrationfiltered off
  6. customdried
  7. customwas recovered

Sources & evidence

ORD record
ord-762575bab4c941288d1ca48bb5356896
Source dataset
uspto-grants-1998_07
Patent number
US05786379

Reaction notes

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