4-Methoxybenzyl alcohol → 4-((4-Methoxybenzyl)oxy)-2-methylene-4-oxobutanoic acid

HRID 2165338Notes

Reaction equation

HRID 2165338 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][C:2]1=[CH2:3].[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][OH:16])=[CH:13][CH:12]=1>CCCCCC>[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][O:16][C:5]([CH2:4][C:2]([C:1]([OH:8])=[O:7])=[CH2:3])=[O:6])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 77384-Methoxybenzyl alcoholHCID 75110Itaconic Anhydride

Product 1

HCID 15126774-((4-Methoxybenzyl)oxy)-2-methylene-4-oxobutanoic acidYield 61%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A 250 ml one-necked round bottomed flask equipped with reflux condenser, nitrogen inlet, and magnetic stir bar was charged with itaconic anhydride (33.6 g, 0.3 mol) toluene (100 ml) and 4-methoxybenzyl alcohol (41.5 g, 0.3 mol). The solution was then warmed to reflux for 60 minutes and then cooled to room temperature. The solution was poured into a 500 ml Erlenmeyer flask, diluted with 100 ml of hexane and allowed to stand whereupon crystals of pure monoester formed. The product was isolated by filtration on a Buchner funnel and air dried to give 45.4 g, 61% of material with mp 83°-85° C., a second crop, 12.9 g, 17% was isolated after cooling of the filtrate in an ice bath.

Workup

  1. customA 250 ml one-necked round bottomed flask equipped
  2. temperaturewith reflux condenser, nitrogen inlet, and magnetic stir bar
  3. temperatureThe solution was then warmed
  4. temperatureto reflux for 60 minutes
  5. additionThe solution was poured into a 500 ml Erlenmeyer flask
  6. customformed
  7. customThe product was isolated by filtration on a Buchner funnel and air
  8. customdried

Sources & evidence

ORD record
ord-e55f0a0671fd4759a2b868d4d9a5a9d7
Source dataset
uspto-grants-1990_07
Patent number
US04939288

Reaction notes

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