Acetic Acid → HCID 19029777, compound

HRID 2260163Notes

Reaction equation

HRID 2260163 reaction equation
[OH:1][C:2]1[CH:17]=[C:16]([O:18][CH2:19][CH:20](OC(=O)C)[C:21]2[CH:30]=[CH:29][C:28]3[C:27]([CH3:32])([CH3:31])[CH2:26][CH2:25][C:24]([CH3:34])([CH3:33])[C:23]=3[CH:22]=2)[CH:15]=[CH:14][C:3]=1[C:4]([O:6]CC1C=CC=CC=1)=[O:5].C(O)C.C(O)(=O)C>[Pd].CCCCCC>[OH:1][C:2]1[CH:17]=[C:16]([O:18][CH2:19][CH2:20][C:21]2[CH:30]=[CH:29][C:28]3[C:27]([CH3:32])([CH3:31])[CH2:26][CH2:25][C:24]([CH3:34])([CH3:33])[C:23]=3[CH:22]=2)[CH:15]=[CH:14][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 702EthanolHCID 19029783HCID 19029783, compound

Product 1

HCID 19029777HCID 19029777, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8058HexaneSolvent

Procedure

2 g (3.89 mmol) of benzyl 2-hydroxy-4-[2-acetoxy-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)ethoxy]benzoate obtained in Example 5(a), 100 ml of ethanol, 10 ml of acetic acid and 1.2 g of palladium on charcoal (10% to 50% water) are introduced into a reactor. The mixture is hydrogenated at 70° C., under a pressure of 7 bar, for 4 hours. The catalyst is filtered and washed with ethanol, and the filtrate is evaporated. The residue obtained is taken up in hexane, filtered and dried. 650 mg (46%) of the expected product of melting point 210°-212° C. are obtained.

Workup

  1. filtrationThe catalyst is filtered
  2. washwashed with ethanol
  3. customthe filtrate is evaporated
  4. customThe residue obtained
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-b177135b93b2471fa96ff0eb9066be7b
Source dataset
uspto-grants-1995_12
Patent number
US05476860

Reaction notes

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