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

HRID 2163262

Reaction equation

HRID 2163262 reaction equation
[OH:1][CH2:2][C:3]1[O:4][CH:5]=[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]>CC(C)=O.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[O:4][CH:5]=[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 233448552-Hydroxymethyl-3-(5-carboethoxypentyloxy)-4-pyrone

Product 1

HCID 233448502-Formyl-3-(5-carboethoxypentyloxy)-4-pyrone

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Procedure

To a solution of 6.35 g (0.022 mole) of 2-hydroxymethyl-3-(5-carboethoxypentyloxy)-4-pyrone in 250 ml of acetone 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. The oil was triturated with hexane/ether to give the crystalline aldehyde, 2-formyl-3-(5-carboethoxypentyloxy)-4- pyrone, weighing 4.1 g (65%), m.p. 32-34.5°.

Workup

  1. filtrationwas filtered
  2. customthe filtrate evaporated to an oil
  3. customThe oil was triturated with hexane/ether

Sources & evidence

ORD record
ord-0432a924a0b249439b7a8bca4f8c889b
Source dataset
uspto-grants-1979_01
Patent number
US04132847

Linked notes

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