p-Toluenesulfonic acid → HCID 54043420, compound

HRID 365218Notes

Reaction equation

HRID 365218 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([OH:9])C=[CH:5][C:3]=1[OH:4].[CH3:10][C:11](=[CH2:19])[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16].[C:20]1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC>[OH:9][C:7]1[CH:8]=[C:2]([CH3:1])[C:3]([OH:4])=[CH:5][C:19]=1[C:11]([CH3:20])([CH3:10])[CH2:12][CH:13]=[CH:14][C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7253MethylhydroquinoneHCID 642298methyl 5-methylhex-5-enoate

Product 1

HCID 54043420HCID 54043420, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

12.4 Parts of 2-methylhydroquinone, 14.2 parts of methyl 5-methylhex-5-enoate, and 0.5 parts of p-toluene sulphonic acid are heated on a steam bath for 24 hours. The cooled reaction mixture is treated with ether, washed firstly with a 10% aqueous solution of sodium hydroxide, and then with water until the aqueous phase is neutral. The ethereal layer is separated and evaporated to give a viscous oil which after short-path distillion at 0.13 mb gives methyl 5-(2',5'-dihydroxy-4'-methyl-phenyl)-5-methyl-hexenoate with the following percentage composition by weight.

Workup

  1. customThe cooled reaction mixture
  2. washwashed firstly with a 10% aqueous solution of sodium hydroxide
  3. customThe ethereal layer is separated
  4. customevaporated
  5. customto give a viscous oil which after short-path distillion at 0.13 mb

Sources & evidence

ORD record
ord-9fea13926cac4c5880ade0e8d71a611f
Source dataset
uspto-grants-1986_08
Patent number
US04608435

Reaction notes

Loading…