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

HRID 443661Notes

Reaction equation

HRID 443661 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].C(OO)(C)(C)C.Cl>C(OO)(C)(C)C>[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

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6410tert-Butyl hydroperoxideHCID 123741,6-HexanediolHCID 314052,6-Di-tert-butylphenolHCID 5360545Sodium2×

Product 1

HCID 211993774-(6-Hydroxyhexyl)-2,6-di-t-butylphenolYield 60.5%

Reagents, catalysts & solvents 1

HCID 6410tert-Butyl hydroperoxideCatalyst

Procedure

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. The flask was purged with nitrogen and there was then added 20.6 grams of 2,6-di-tert.-butylphenol (0.1 moles) and 0.5 grams (0.0055 moles) of tert.-butyl hydroperoxide. The mixture was heated at 230° C. for 5.5 hours with 0.5 gram increments of tert.-butyl hydroperoxide being added after 1, 2.5, 3.5, and 4.5 hours. The mixture was allowed to cool and was then neutralized by the addition of 5 ml. of concentrated hydrochloric acid. Sodium chloride from the neutralization of the base was removed by filtration and the filtrate was distilled under vacuum. There was obtained 18.5 grams 6-(3,5-di-tert.-butyl-4-hydroxyphenyl)hexanol, 60.5% yield.

Workup

  1. customflask fitted with a water trap
  2. dissolutiondissolved
  3. customThe flask was purged with nitrogen and there
  4. additionadded after 1, 2.5, 3.5, and 4.5 hours
  5. temperatureto cool
  6. additionwas then neutralized by the addition of 5 ml
  7. customSodium chloride from the neutralization of the base was removed by filtration
  8. distillationthe filtrate was distilled under vacuum

Sources & evidence

ORD record
ord-8cda7c210e4d4492b48b7c2fa963a61d
Source dataset
uspto-grants-1981_04
Patent number
US04260832

Reaction notes

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