Ethanol → HCID 20040624, compound

HRID 1388202Notes

Reaction equation

HRID 1388202 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][C:7]([C:10]1[CH:16]=[C:15]([OH:17])[C:14]([C:18]([CH3:26])([CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[CH3:19])=[CH:13][C:11]=1[OH:12])([CH3:9])[CH3:8])([OH:3])=[O:2].[CH2:27](O)[CH3:28].S(=O)(=O)(O)O.[CH3:35][CH2:36]OCC>>[CH2:35]([O:2][C:1]([CH2:4][CH2:5][CH2:6][C:7]([C:10]1[CH:16]=[C:15]([OH:17])[C:14]([C:18]([CH3:26])([CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:27][CH3:28])=[O:24])[CH3:19])=[CH:13][C:11]=1[OH:12])([CH3:9])[CH3:8])=[O:3])[CH3:36]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 20040604HCID 20040604, compound

Product 1

HCID 20040624HCID 20040624, compound

Procedure

5.0 Parts of 2,5-bis-(5-carboxy-2-methylpent-2-yl)-hydroquinone, 100 parts of absolute ethanol, and 1.0 parts of 98% sulphuric acid are refluxed for 16 hours. The solution is then stripped down under reduced pressure, the residue taken up in ether, and washed with sodium bicarbonate solution. The ethereal solution after being concentrated and diluted with 40°-60° petroleum ether yields 2,5-bis-(5-ethoxycarbonyl-2-methylpent-2-yl)-hydroquinone, [formula (103)] m.p. 146°-149° C. with the following percentage composition by weight:

Workup

  1. washwashed with sodium bicarbonate solution
  2. concentrationThe ethereal solution after being concentrated
  3. additiondiluted with 40°-60° petroleum ether

Sources & evidence

ORD record
ord-324b44500f4d4290bb83f138e1ce7a60
Source dataset
uspto-grants-1984_02
Patent number
US04430425

Reaction notes

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