Dibutylamine → HCID 20258786, compound

HRID 1583523Notes

Reaction equation

HRID 1583523 reaction equation
O.[C:2]1([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=[C:4](O)[CH:3]=1.[CH2:11]([NH:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH3:14]>>[CH2:11]([N:15]([CH2:16][CH2:17][CH2:18][CH3:19])[C:4]1[CH:3]=[C:2]([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=1)[CH2:12][CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 8148DibutylamineHCID 3083941Resorcinol, 5-methyl-, monohydrate

Product 1

HCID 20258786HCID 20258786, compoundYield 61%

Conditions

Temperature
200 °C

Procedure

A 300 milliliter Parr minibomb was charged with orcinol monohydrate, 42 grams, 0.3 mole and di-n-butylamine, 128 milliliters. The bomb was sealed and heated to 200° C. At this temperature the internal pressure of the bomb was 90 pounds per square inch as registered on the gauge. After 48 hours at 200°, the bomb was cooled and the light brown syrup analyzed by thin-layer chromatography. The excess di-n-butylamine was removed by distillation at 20 Torr and the product was further purified by filtration through a silica gel column using ethyl acetate as the eluent. The product 3-dibutylamino-5-methylphenol was isolated in 61% yield: 43 grams. This material was not further characterized but used directly in the subsequent reaction.

Workup

  1. customThe bomb was sealed
  2. temperaturethe bomb was cooled
  3. customThe excess di-n-butylamine was removed by distillation at 20 Torr
  4. filtrationthe product was further purified by filtration through a silica gel column

Sources & evidence

ORD record
ord-b999a32ba9e34272a7863c8ed61cc6b2
Source dataset
uspto-grants-1985_11
Patent number
US04552822

Reaction notes

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