1,4-Dioxane → HCID 9820533, compound

HRID 274026Notes

Reaction equation

HRID 274026 reaction equation
[CH3:1][C:2]1([CH3:34])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH2:14][C:15]([O:17][C:18]3[CH:33]=[CH:32][C:21]([C:22]([O:24]CC4C=CC=CC=4)=[O:23])=[CH:20][CH:19]=3)=[O:16])[CH:5]=[CH:4][C:3]1=2.O1CCOCC1>[Pd].C(OCC)C>[CH3:1][C:2]1([CH3:34])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([CH2:14][C:15]([O:17][C:18]3[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:32][CH:33]=3)=[O:16])[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 54251739HCID 54251739, compound

Product 1

HCID 9820533HCID 9820533, compoundYield 70.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

2.4 g (5.2 mmol) of benzyl 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylacetoxy)benzoate, 1 g of palladium on charcoal (5%) and 100 ml of dioxane are introduced into a reactor. The mixture is hydrogenated at room temperature and under a pressure of 7 bars for three hours, the catalyst is filtered off and washed with twice 50 ml of THF and the filtrates are evaporated. The residue obtained is ground in the minimum amount of ethyl ether, filtered off and dried. 1.35 g (70%) of 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylacetoxy)benzoic acid, melting point 142°-143° C., are obtained.

Workup

  1. filtrationthe catalyst is filtered off
  2. washwashed with twice 50 ml of THF
  3. customthe filtrates are evaporated
  4. customThe residue obtained
  5. filtrationfiltered off
  6. customdried

Sources & evidence

ORD record
ord-efdb12aa93bb45128385716a457e1e1f
Source dataset
uspto-grants-1995_02
Patent number
US05387594

Reaction notes

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