Methyl rac-1,2,3,4,5,8-hexahydro-5,8-dioxonaphthalene-2-carboxylate → Methyl rac-5,8-dihydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate

HRID 647643Notes

Reaction equation

HRID 647643 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9](=[O:12])[C:8]2[CH2:7][CH:6]([C:13]([O:15][CH3:16])=[O:14])[CH2:5][CH2:4][C:3]1=2.[H][H]>[Pd].CO>[OH:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH2:4][CH2:5][CH:6]([C:13]([O:15][CH3:16])=[O:14])[CH2:7]2

Participants

5

Reactant 2

HCID 20283297Methyl rac-1,2,3,4,5,8-hexahydro-5,8-dioxonaphthalene-2-carboxylateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 20283289Methyl rac-5,8-dihydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylateYield 102.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.30 g of 10% palladium-on-carbon catalyst was added to a solution of 4.0 g (0.018 mol) of methyl rac-1,2,3,4,5,8-hexahydro-5,8-dioxonaphthalene-2-carboxylate in 180 ml of methanol and the mixture was shaken under one atmosphere of hydrogen until hydrogen uptake ceased (429 ml, 18 minutes). The mixture was filtered and the filtrate was evaporated to yield 4.1 g (100%) of methyl rac-5,8-dihydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate in the form of a white crystalline solid of melting point 135°-136° C.

Workup

  1. custom(429 ml, 18 minutes)
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-18ad673f16354efa9026237a304abed7
Source dataset
uspto-grants-1983_10
Patent number
US04409391

Reaction notes

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