2-Hydroxymethyl-6-methyl-3-(5-carboethoxypentyloxy)-4-pyrone → 2-Formyl-6-methyl-3-(5-carboethoxypentyloxy)-4-pyrone

HRID 2163270Notes

Reaction equation

HRID 2163270 reaction equation
[OH:1][CH2:2][C:3]1[O:4][C:5]([CH3:21])=[CH:6][C:7](=[O:20])[C:8]=1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(#N)C.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[O:4][C:5]([CH3:21])=[CH:6][C:7](=[O:20])[C:8]=1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:1]

Participants

4

Reactant 1

HCID 233448582-Hydroxymethyl-6-methyl-3-(5-carboethoxypentyloxy)-4-pyrone

Product 1

HCID 233448572-Formyl-6-methyl-3-(5-carboethoxypentyloxy)-4-pyrone

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4.25 g of 2-hydroxymethyl-6-methyl-3-(5-carboethoxypentyloxy)-4-pyrone in 110 ml of acetonitrile was added 12 g of activated manganese dioxide. The resulting suspension was stirred for 3 hr, at which time the mixture was filtered and the filtrate evaporated to an oil, 2-formyl-6-methyl-3-(5-carboethoxypentyloxy)-4-pyrone, weighing 4.0 g (94%). NMR (CDCl3): δ1.23 (3H, t, J = 7 Hz), 2.36 (3H, s), 6.32 (1H, s).

Workup

  1. filtrationwas filtered
  2. customthe filtrate evaporated to an oil, 2-formyl-6-methyl-3-(5-carboethoxypentyloxy)-4-pyrone

Sources & evidence

ORD record
ord-72eba00a17534b8688c0c91efe29c73e
Source dataset
uspto-grants-1979_01
Patent number
US04132847

Reaction notes

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