5-(Hydroxymethyl)furfural → 2-Furanmethanol, 5-(dimethoxymethyl)-

HRID 1756167Notes

Reaction equation

HRID 1756167 reaction equation
[OH:1][CH2:2][C:3]1[O:7][C:6]([CH:8]=[O:9])=[CH:5][CH:4]=1.[CH:10]([O-])([O-])[O:11]C.[C:15]1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(=O)(O)[O-].[Na+]>CO.O.C(OCC)C>[CH3:15][O:9][CH:8]([O:11][CH3:10])[C:6]1[O:7][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=1

Participants

8

Reactant 4

HCID 2373325-(Hydroxymethyl)furfuralHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 53629101Methylorthoformate

Product 1

HCID 5881272-Furanmethanol, 5-(dimethoxymethyl)-

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

16.8 g of 5-hydroxymethyl-2-furaldehyde was dissolved in 70 ml of methanol, and 14.7 ml of methyl orthoformate and 170 mg of pyridinium p-toluenesulfonate were added. After the mixture was stirred at room temperature for 2 hours, 350 mg of sodium bicarbonate was added. The solution was stirred at room temperature for 30 minutes, and then ethyl ether and water were added. The organic layer separated was worked up in a customary manner to give 21.6 g of 5-hydroxymethyl-2-furaldehyde dimethylacetal as a pale brown oil.

Workup

  1. stirringThe solution was stirred at room temperature for 30 minutes
  2. customThe organic layer separated

Sources & evidence

ORD record
ord-d53e4499a45a420f95c6b0752a5c3cd1
Source dataset
uspto-grants-1995_08
Patent number
US05439932

Reaction notes

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