Diethyl Ether → HCID 20040612, compound

HRID 1388203Notes

Reaction equation

HRID 1388203 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH2:7][C:8]([C:11]1[CH:17]=[C:16]([OH:18])[C:15]([C:19]([CH3:28])([CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH3:20])=[CH:14][C:12]=1[OH:13])([CH3:10])[CH3:9])=[O:4].C(O)[C:30]1[O:34][CH:33]=[CH:32][CH:31]=1.C[O-].[Na+].[CH3:39][CH2:40][O:41][CH2:42][CH3:43]>>[CH2:1]([O:2][C:3]([CH2:5][CH2:6][CH2:7][C:8]([C:11]1[CH:17]=[C:16]([OH:18])[C:15]([C:19]([CH3:28])([CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][C:33]2[O:34][CH:30]=[CH:31][CH:32]=2)=[O:25])[CH3:20])=[CH:14][C:12]=1[OH:13])([CH3:10])[CH3:9])=[O:4])[C:42]1[O:41][CH:40]=[CH:39][CH:43]=1

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 7361Furfuryl AlcoholHCID 10942334Sodium MethoxideHCID 20040579HCID 20040579, compound

Product 1

HCID 20040612HCID 20040612, compound

Procedure

8.0 Parts of 2,5-bis-(5-methoxycarbonyl-2-methyl-pent-2-yl)-hydroquinone, 100 parts of furfuryl alcohol and 1.0 parts of sodium methoxide are heated on a steam-bath for 24 hours. The cooled reaction mixture is diluted with ether and washed with water. After removing the ether and excess furfuryl alcohol, the residue is triturated with 40°-60° petroleum ether containing ether to yield 2,5-bis-(5-furfuryloxycarbonyl-2-methyl-pent-2-yl)-hydroquinone, [formula (123)] m.p. 139°-142° C. Crystallisation from methanol containing 5% water yields crystals of m.p. 140°-143° C. with the following percentage composition by weight:

Workup

  1. customThe cooled reaction mixture
  2. washwashed with water
  3. customAfter removing the ether and excess furfuryl alcohol
  4. customthe residue is triturated with 40°-60° petroleum ether
  5. additioncontaining ether

Sources & evidence

ORD record
ord-8cabad1fc8b740848b34cf447c7e0405
Source dataset
uspto-grants-1984_02
Patent number
US04430425

Reaction notes

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