Hydrochloric Acid → 4-Dodecylresorcinol

HRID 1904029Notes

Reaction equation

HRID 1904029 reaction equation
[C:1]([C:14]1[CH:20]=[CH:19][C:17]([OH:18])=[CH:16][C:15]=1[OH:21])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].Cl.O>C(O)(=O)C.C(Cl)(Cl)Cl.[Zn].[Hg](Cl)Cl>[CH2:1]([C:14]1[CH:20]=[CH:19][C:17]([OH:18])=[CH:16][C:15]=1[OH:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

8

Reactant 3

HCID 313Hydrochloric Acid3×HCID 962WaterHCID 2455351-(2,4-dihydroxyphenyl)dodecan-1-one

Product 1

HCID 904584-Dodecylresorcinol

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 24085Mercuric ChlorideCatalystHCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

29.2 g of the product from (i) in 200 ml of acetic acid was added to 300 ml of 6 M hydrochloric acid to give a fine precipitate. To this was assed a zinc amalgam (made by intimately mixing 60 g of zinc, 6 g of mercury (II) chloride, 5 ml of conc. hydrochloric acid and 90 ml of water over 20 minutes. The mixture was heated at reflux for 5 hours; three further portions of 60 ml of conc. hydrochloric acid being added. After cooling, the filtered solids were taken up in chloroform, refiltered, and washed with 6 M hydrochloric acid, then water, dried and evaporated to give 26 g of the crude product. This was recrystallised from light petroleum (b.p. 60°-80° C.) to give 22.9 g of the product with a melting point of from 81°-82.5° C.

Workup

  1. customto give a fine precipitate
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 5 hours
  4. temperatureAfter cooling
  5. washwashed with 6 M hydrochloric acid
  6. dry with materialwater, dried
  7. customevaporated
  8. customto give 26 g of the crude product
  9. customThis was recrystallised from light petroleum (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-926111bfe3e74469a269550f8f09fb4e
Source dataset
uspto-grants-1984_03
Patent number
US04439518

Reaction notes

Loading…