Sodium Dithionite → (E)-5-(2,5-dihydroxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl benzoate

HRID 1195473Notes

Reaction equation

HRID 1195473 reaction equation
[C:1]([O:9][CH2:10]/[CH:11]=[C:12](\[CH3:26])/[CH2:13][CH2:14][C:15]1[C:20](=[O:21])[C:19]([CH3:22])=[C:18]([CH3:23])[C:17](=[O:24])[C:16]=1[CH3:25])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>C1COCC1.O>[C:1]([O:9][CH2:10]/[CH:11]=[C:12](\[CH3:26])/[CH2:13][CH2:14][C:15]1[C:16]([CH3:25])=[C:17]([OH:24])[C:18]([CH3:23])=[C:19]([CH3:22])[C:20]=1[OH:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 67900681(E)-3-methyl-5-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)-2-pentenyl benzoate

Product 1

HCID 86745748(E)-5-(2,5-dihydroxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl benzoateYield 84.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.22 g (3.5 mmol) of (E)-3-methyl-5-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)-2-pentenyl benzoate in 10 ml of THF was treated dropwise with a solution of 0.9 g of sodium dithionite in 8 ml of water. After 1 hour the mixture was extracted with chloroform (2 x) and the combined extracts were washed three times with water. The residue remaining after removal of the solvent was washed with hexane and dried under vacuum, yielding 1.05 g of colourless (E)-5-(2,5-dihydroxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl benzoate. M.P. 112°-114° C.

Workup

  1. extractionAfter 1 hour the mixture was extracted with chloroform (2 x)
  2. washthe combined extracts were washed three times with water
  3. customafter removal of the solvent
  4. washwas washed with hexane
  5. customdried under vacuum

Sources & evidence

ORD record
ord-ad3e34a8875d45adb1cadf8d3c54d752
Source dataset
uspto-grants-1992_05
Patent number
US05110955

Reaction notes

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