1,3,5-Cyclohexanetriol, 2,2,4,4,6,6-hexamethyl- → 1,3,5-tris-[3-(3,5-Di-t-butyl-4-hydroxyphenyl)-propionyloxy]-2,2,4,4,6,6-hexamethylcyclohexane

HRID 1657952Notes

Reaction equation

HRID 1657952 reaction equation
[CH3:1][C:2]1([CH3:15])[CH:7]([OH:8])[C:6]([CH3:10])([CH3:9])[CH:5]([OH:11])[C:4]([CH3:13])([CH3:12])[CH:3]1[OH:14].[C:16]([C:20]1[CH:21]=[C:22]([CH2:31][CH2:32][C:33](Cl)=[O:34])[CH:23]=[C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:25]=1[OH:26])([CH3:19])([CH3:18])[CH3:17]>N1C=CC=CC=1>[C:16]([C:20]1[CH:21]=[C:22]([CH2:31][CH2:32][C:33]([O:14][CH:3]2[C:2]([CH3:15])([CH3:1])[CH:7]([O:8][C:33](=[O:34])[CH2:32][CH2:31][C:22]3[CH:23]=[C:24]([C:27]([CH3:28])([CH3:30])[CH3:29])[C:25]([OH:26])=[C:20]([C:16]([CH3:19])([CH3:17])[CH3:18])[CH:21]=3)[C:6]([CH3:9])([CH3:10])[CH:5]([O:11][C:33](=[O:34])[CH2:32][CH2:31][C:22]3[CH:23]=[C:24]([C:27]([CH3:28])([CH3:30])[CH3:29])[C:25]([OH:26])=[C:20]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:21]=3)[C:4]2([CH3:13])[CH3:12])=[O:34])[CH:23]=[C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:25]=1[OH:26])([CH3:19])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 5201261,3,5-Cyclohexanetriol, 2,2,4,4,6,6-hexamethyl-HCID 156069683-(3,5-Di-tert-butyl-4-hydroxyphenyl)propionyl chloride

Product 1

HCID 215321481,3,5-tris-[3-(3,5-Di-t-butyl-4-hydroxyphenyl)-propionyloxy]-2,2,4,4,6,6-hexamethylcyclohexane

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred cooled solution of 2.16 g (0.010 mole) of 2,2,4,4,6,6-hexamethyl cyclohexane-1,3,5-triol in 50 ml of pyridine is added in several portions over a 20 minute period, 10.69 g (0.036 mole) of 3-(3,5-di-t-butyl-4hydroxyphenyl)propionyl chloride. This mixture is stirred for 30 minutes at 0° to 5°C and then for 15 hours at 45° to 50°C. The mixture is cooled to room temperature and poured into ice water. This mixture is then extracted several times with ethyl ether and these extracts are in turn washed with 2N sulfuric acid, water, 5% aqueous sodium carbonate solution, water and finally saturated sodium chloride solution. The ethereal extracts are then dried over sodium sulfate and evaporated to yield the product. Further purification is achieved by means of chromatography through silica gel, eluting successively with heptane and benzene. Removal of solvent and drying to constant weight at 100°/0.1 mm affords the product, m.p. 105°-115°C.

Workup

  1. additionis added in several portions over a 20 minute period
  2. waitfor 15 hours at 45° to 50°C
  3. extractionThis mixture is then extracted several times with ethyl ether
  4. washwashed with 2N sulfuric acid, water, 5% aqueous sodium carbonate solution, water and finally saturated sodium chloride solution
  5. dry with materialThe ethereal extracts are then dried over sodium sulfate
  6. customevaporated
  7. customto yield the product
  8. customFurther purification
  9. washeluting successively with heptane and benzene
  10. customRemoval of solvent
  11. customdrying to constant weight at 100°/0.1 mm
  12. customaffords the product, m.p. 105°-115°C.

Sources & evidence

ORD record
ord-ac29170e666641b3b4ed8020d53191fb
Source dataset
uspto-grants-1976_06
Patent number
US03962313

Reaction notes

Loading…