Lauric Acid → 1-(2,4-dihydroxyphenyl)dodecan-1-one

HRID 1904028Notes

Reaction equation

HRID 1904028 reaction equation
[C:1](O)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Cl-].[Ca+2].[Cl-].[C:18]1([CH:25]=[CH:24][CH:23]=[C:21]([OH:22])[CH:20]=1)[OH:19].C(Cl)(Cl)Cl>O.[Cl-].[Zn+2].[Cl-]>[C:1]([C:23]1[CH:24]=[CH:25][C:18]([OH:19])=[CH:20][C:21]=1[OH:22])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 3893Lauric AcidHCID 5054ResorcinolHCID 6212ChloroformHCID 5284359Calcium Chloride

Product 1

HCID 2455351-(2,4-dihydroxyphenyl)dodecan-1-oneYield 41.4%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Procedure

68 g of granular zinc chloride and 250 g of lauric acid were melted togerther at 125° C., under nitrogen and with protection from moisture by calcium chloride. The mass was stirred and 55 g of resorcinol were added portionwise over 15 minutes. The mixture was stirred a further 2 hours, cooled and drowned in 500 ml of water. 100 ml of chloroform was added to break up the solid mass, and the crystalline solid remaining was filtered, washed with chloroform, then water, to give 60.4 g of a solid with a melting point of from 79°-83° C. This was used without further purification. The analytical sample was recrystallised from light petroleum (b.p. 60°-80° C.). The pure product had a melting point of from 83.5°-85° C.

Workup

  1. stirringThe mixture was stirred a further 2 hours
  2. temperaturecooled
  3. filtrationthe crystalline solid remaining was filtered
  4. washwashed with chloroform

Sources & evidence

ORD record
ord-45985a38a8c64f5d8fa365875ca0bbb5
Source dataset
uspto-grants-1984_03
Patent number
US04439518

Reaction notes

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