Water → 5-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one

HRID 1249594Notes

Reaction equation

HRID 1249594 reaction equation
[OH:1][CH2:2][C:3]1[O:4][CH:5]=[C:6]([OH:10])[C:7](=[O:9])[CH:8]=1.[OH-].[Na+].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CO>[OH:1][CH2:2][C:3]1[O:4][CH:5]=[C:6]([O:10][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:7](=[O:9])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3840Kojic AcidHCID 7503Benzyl ChlorideHCID 14798Sodium Hydroxide

Product 1

HCID 9015985-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A suspension of 2-(hydroxymethyl)-5-hydroxy-4H-pyran-4-one (56.8 g, 0.4 mole) in 400 ml of methanol was treated with sodium hydroxide (16 g, 0.4 mole) in 200 ml of warm methanol followed by 50.6 g (46 ml, 0.4 mole) of benzyl chloride. The mixture was heated to reflux for 3.5 hours, cooled, and poured into 1 L of water. The resulting solid was filtered and washed with ca. 1.5 L of water, 200 ml of ethanol and 400 ml of hexane. After drying under high vacuum, the weight of product was 55.7 g.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3.5 hours
  3. temperaturecooled
  4. filtrationThe resulting solid was filtered
  5. washwashed with ca. 1.5 L of water, 200 ml of ethanol and 400 ml of hexane
  6. customAfter drying under high vacuum

Sources & evidence

ORD record
ord-20d81937903747e4b9f06e0c2ca87f86
Source dataset
uspto-grants-1986_12
Patent number
US04632985

Reaction notes

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