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

HRID 1195471Notes

Reaction equation

HRID 1195471 reaction equation
[C:1]([O:4][CH2:5]/[CH:6]=[C:7](\[CH3:21])/[CH2:8][CH2:9][C:10]1[C:15](=[O:16])[C:14]([CH3:17])=[C:13]([CH3:18])[C:12](=[O:19])[C:11]=1[CH3:20])(=[O:3])[CH3:2].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C1COCC1.O>[C:1]([O:4][CH2:5]/[CH:6]=[C:7](\[CH3:21])/[CH2:8][CH2:9][C:10]1[C:11]([CH3:20])=[C:12]([OH:19])[C:13]([CH3:18])=[C:14]([CH3:17])[C:15]=1[OH:16])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 19819053(E)-3-methyl-5-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)-2-pentenyl acetate

Product 1

HCID 19819049(E)-5-(2,5-dihydroxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetateYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.27 g (11.3 mmol) of (E)-3-methyl-5-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)-2-pentenyl acetate in 60 ml of THF was treated dropwise with 40 ml of a freshly Prepared 0.5M sodium dithionite solution. After completion of the addition the mixture was diluted with water and extracted with chloroform. The combined extracts were washed with water and freed from solvent. The solid residue was washed with hexane and dried under oil pump vacuum, yielding 2.94 g of (E)-5-(2,5-dihydroxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate as a colourless powder; m.p. 94.5°-96° C.

Workup

  1. additionAfter completion of the addition the mixture
  2. extractionextracted with chloroform
  3. washThe combined extracts were washed with water
  4. washThe solid residue was washed with hexane
  5. customdried under oil pump vacuum

Sources & evidence

ORD record
ord-21f019550d9b4e37a2cf0f45b9a58035
Source dataset
uspto-grants-1992_05
Patent number
US05110955

Reaction notes

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