Hydrochloric Acid → 1,3-Benzenediol, 2-hexyl-

HRID 1032741Notes

Reaction equation

HRID 1032741 reaction equation
Cl.O.[C:3]([C:10]1[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][C:11]=1[OH:12])(=O)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>[Zn].C1(C)C=CC=CC=1>[CH2:3]([C:10]1[C:11]([OH:12])=[CH:13][CH:14]=[CH:15][C:16]=1[OH:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid3×HCID 962Water2×HCID 12364060HCID 12364060, compound

Product 1

HCID 30143741,3-Benzenediol, 2-hexyl-

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 1140TolueneSolvent

Procedure

Subsequently, 30.0 g of zinc powder was mixed with 2.50 g of mercuric chloride, 1.5 ml of concentrated hydrochloric acid and 38 ml of water and shaken for 5 minutes, followed by decantation to discard the aqueous phase. Thereafter, 20 ml of water, 45 ml of concentrated hydrochloric acid, 25 ml of toluene and 14.6 g of the previously obtained n-hexanoyl resorcinol were added in this order, followed by refluxing under heating conditions for 30 hours. During the refluxing, 12.5 ml of concentrated hydrochloric acid was added four times every 6 hours in order to keep the concentration of the acid. The reaction solution was cooled down to room temperature and subjected to liquid separation. The resultant aqueous phase was extracted three times with 50 ml of isopropyl ether and combined with the organic phase, followed by washing with 100 ml of water. The solvent was distilled off by means of an evaporator and the residue was crystallized from n-hexane to obtain 4.3 g of n-hexyl resorcinol as colorless needle crystals.

Workup

  1. temperatureby refluxing under heating conditions for 30 hours
  2. customsubjected to liquid separation
  3. extractionThe resultant aqueous phase was extracted three times with 50 ml of isopropyl ether
  4. washby washing with 100 ml of water
  5. distillationThe solvent was distilled off by means of an evaporator
  6. customthe residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-d62d5debfcd44af18325fe62be2dbeca
Source dataset
uspto-grants-1990_09
Patent number
US04959393

Reaction notes

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