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

HRID 1464777Notes

Reaction equation

HRID 1464777 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-5b47d8919a65412297a660ee84b31f52
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

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