2-Methylbenzenesulfonic acid → HCID 20040641, compound

HRID 1388204Notes

Reaction equation

HRID 1388204 reaction equation
[C:1]([C:5]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=1[OH:7])([CH3:4])([CH3:3])[CH3:2].CC(=C)C[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19].[C:23]1([CH3:33])[C:24](S(O)(=O)=O)=CC=C[CH:28]=1>CCOCC>[C:23]([C:9]1[C:10]([OH:12])=[CH:11][C:5]([C:1]([CH3:4])([CH3:2])[CH2:3][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[C:6]([OH:7])[CH:8]=1)([CH3:33])([CH3:24])[CH3:28]

Participants

5

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 16043Tert-ButylhydroquinoneHCID 642298methyl 5-methylhex-5-enoate

Product 1

HCID 20040641HCID 20040641, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

16.6 Parts of 2-t-butylhydroquinone, 14.2 parts of methyl 5-methyl-hex-5-enoate and 0.5 part of p.toluene sulphonic acid are heated on a steam-bath for 24 hours. The reaction mixture is then taken up in ether, washed with dilute sodium hydroxide solution, and then with water. After removing ether and lower boilers, distillation gave methyl 5-(4-t-butyl-2,5-dihydroxy-phenyl)-5-methyl-hexanoate, [formula (124)], b0.3 186°-210° C. This fraction after crystallisation from petroleum ether, had a m.p. 136°-139° C. and the following percentage composition by weight:

Workup

  1. washwashed with dilute sodium hydroxide solution
  2. customAfter removing
  3. distillationether and lower boilers, distillation

Sources & evidence

ORD record
ord-64794ae8d9bb4b94bfcfd9c20b4b3cce
Source dataset
uspto-grants-1984_02
Patent number
US04430425

Reaction notes

Loading…