Trimethylhydroquinone → HCID 13633545, compound

HRID 978913Notes

Reaction equation

HRID 978913 reaction equation
[CH3:1][C:2]1[C:3]([OH:11])=[C:4]([CH3:10])[C:5]([CH3:9])=[C:6]([CH:8]=1)[OH:7].Cl[CH2:13][CH:14]=[C:15]([CH3:35])[CH2:16][CH2:17][CH2:18][C:19]([Cl:34])([CH3:33])[CH2:20][CH2:21][CH2:22][C:23]([Cl:32])([CH3:31])[CH2:24][CH2:25][CH2:26][C:27]([Cl:30])([CH3:29])[CH3:28].[Cl-].[NH4+]>O1CCOCC1>[CH3:35][C:15]1([CH2:16][CH2:17][CH2:18][C:19]([Cl:34])([CH3:33])[CH2:20][CH2:21][CH2:22][C:23]([Cl:32])([CH3:31])[CH2:24][CH2:25][CH2:26][C:27]([Cl:30])([CH3:29])[CH3:28])[CH2:14][CH2:13][C:8]2[C:6](=[C:5]([CH3:9])[C:4]([CH3:10])=[C:3]([OH:11])[C:2]=2[CH3:1])[O:7]1

Participants

5

Reactant 3

HCID 12785TrimethylhydroquinoneHCID 25517Ammonium ChlorideHCID 54100633HCID 54100633, compound

Product 1

HCID 13633545HCID 13633545, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Fused zinc chloride (0.22 g), trimethylhydroquinone (2.47 g) and anhydrous dioxane (10 cc) are introduced into a 250 cc reactor. The mixture is heated to 40°-45° C. and a solution of 1,7,11,15-tetrachloro-3,7,11,15-tetramethylhexadec-2-ene (6.8 g) in dioxane (7 cc) is then added over the course of 20 minutes. Stirring is continued for 1 hour 30 minutes. This reaction mixture is poured into an aqueous solution (50 cc) of ammonium chloride (100 g/liter). The mixture is extracted with ethyl acetate (twice 50 cc) and the organic phases are then dried over magnesium sulphate. After filtration and evaporation of the solvent, 2,5,7,8-tetramethyl-2-(4',8',12'-trichloro-4',8',12'-trimethyltridecyl)-chroman-6-ol is obtained in a yield of 43.5%.

Workup

  1. temperatureThe mixture is heated to 40°-45° C.
  2. extractionThe mixture is extracted with ethyl acetate (twice 50 cc)
  3. dry with materialthe organic phases are then dried over magnesium sulphate
  4. filtrationAfter filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-c30644bfcb2f4484be25561ee7f427c2
Source dataset
uspto-grants-1987_05
Patent number
US04665244

Reaction notes

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