Hydrochloric Acid → 4-(6-Hydroxyhexyl)-2,6-di-t-butylphenol

HRID 443659Notes

Reaction equation

HRID 443659 reaction equation
[Na].[CH2:2](O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[C:10]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:15]=1[OH:24])([CH3:13])([CH3:12])[CH3:11].Cl>>[C:20]([C:16]1[CH:17]=[C:18]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8])[CH:19]=[C:14]([C:10]([CH3:13])([CH3:12])[CH3:11])[C:15]=1[OH:24])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 123741,6-HexanediolHCID 314052,6-Di-tert-butylphenolHCID 5360545Sodium2×

Product 1

HCID 211993774-(6-Hydroxyhexyl)-2,6-di-t-butylphenolYield 66.6%

Conditions

Temperature
225 °C

Procedure

To 1.15 grams of metallic sodium (0.05 moles) was added to 59 grams of 1,6-hexanediol (0.5 moles) in a 250 ml flask fitted with a water trap and the mixture was stirred until the sodium dissolved. There was then added 20.6 grams of 2,6-di-tert.-butylphenol (0.1 mole) and the mixture was heated for 7.5 hours at 225° C. The mixture was allowed to cool and the base was neutralized by the addition of 5 ml. of concentrated hydrochloric acid. Sodium chloride from neutralization of the base was removed by filtration and the filtrate was distilled under vacuum. There was obtained 20.4 grams (66.6% yield) of 6-(3,5-di-tert.-butyl-4-hydroxyphenyl)hexanol.

Workup

  1. customfitted with a water trap
  2. dissolutiondissolved
  3. temperatureto cool
  4. additionthe base was neutralized by the addition of 5 ml
  5. customSodium chloride from neutralization of the base was removed by filtration
  6. distillationthe filtrate was distilled under vacuum

Sources & evidence

ORD record
ord-587585ab1af74487abede341db9deaa5
Source dataset
uspto-grants-1981_04
Patent number
US04260832

Reaction notes

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