Hydrochloric Acid → 2,6-Bis(2,4-dihydroxy-5-hexylbenzyl)-4-methylphenol

HRID 1004543

Reaktionsgleichung

Reaktionsgleichung von HRID 1004543
[CH2:1]([C:7]1[CH:13]=[CH:12][C:10]([OH:11])=[CH:9][C:8]=1[OH:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].O[CH2:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH2:24]O)[C:18]=1[OH:26].[OH2:27].[C:28]1([CH3:38])[C:29](S(O)(=O)=O)=[CH:30][CH:31]=[CH:32][CH:33]=1.Cl.[OH2:40]>CO>[OH:27][C:31]1[CH:30]=[C:29]([OH:40])[C:28]([CH2:38][CH2:3][CH2:2][CH2:1][CH2:7][CH3:8])=[CH:33][C:32]=1[CH2:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH2:24][C:12]2[CH:13]=[C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:8]([OH:14])=[CH:9][C:10]=2[OH:11])[C:18]=1[OH:26]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 3610HexylresorcinolHCID 70392,6-Dimethylol-p-cresolHCID 124969952-Methylbenzenesulfonic acid hydrate

Produkt 1

HCID 187925472,6-Bis(2,4-dihydroxy-5-hexylbenzyl)-4-methylphenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To 500 ml flask was added 300 ml of methanol, 60 g of 4-hexylresorcinol and 16.9 g of 2,6-bis(hydroxymethyl)-4-methylphenol. 2.2 g of toluenesulfonic acid monohydrate was then added and the reaction solution heated at reflux for 20.5 hours. The warm reaction solution was slowly added, with agitation, to about 1.5 L of de-mineralized water containing about 1.3% hydrochloric acid. To the precipitate mixture an additional 20 ml of concentrated hydrochloric acid was added and mixed until the precipitate solidified. The crude product was collected on a filter, reduced to small pieces and air dried while gently warmed on a hot plate. To the crude product 200 ml of toluene was added and the mixture heated to about 85° C. The hot solution was filtered using a pre-heated Buchner funnel and the filtrate allowed to stand at room temperature. The crystals were collected on the filter, rinsed and slurred in 50 ml of cold toluene. After collection and drying about 16.5 g of product was obtained having a purity of about 95% as determined by HPLC.

Aufarbeitung

  1. temperaturethe reaction solution heated
  2. temperatureat reflux for 20.5 hours
  3. customThe warm reaction solution
  4. additionmixed until the precipitate
  5. customThe crude product was collected on a filter
  6. customdried
  7. temperaturewhile gently warmed on a hot plate
  8. additionTo the crude product 200 ml of toluene was added
  9. filtrationThe hot solution was filtered
  10. customto stand at room temperature
  11. customThe crystals were collected on the filter
  12. washrinsed
  13. customAfter collection
  14. dry with materialdrying about 16.5 g of product
  15. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-c747984da85140ada52d871b3565a4df
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06051358

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