4-Hydroxybenzoic Acid → 4-Undecanoyloxybenzoic acid

HRID 850818Notes

Reaction equation

HRID 850818 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:18](Cl)(=[O:29])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].Cl>CN(C)C1C=CN=CC=1.ClCCl>[C:18]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)(=[O:29])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

7

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 87287Undecanoyl chloride

Product 1

HCID 154568744-Undecanoyloxybenzoic acid

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

12.7 Grams (0.0917 mol) of p-hydroxybenzoic acid was added to 150 ml of dichloromethane, and to this suspension was added 10.2 g (0.0917 mol) of triethylamine. The mixture was stirred until a homogeneous solution was formed. 19.7 Grams (0.096 mol) of undecanoyl chloride was added to the solution at such a rate that the dichloromethane was not refluxed. Then, 1.0 g (0.0085 mol) of 4-dimethylaminopyridine was added, and the mixture was stirred at room temperature overnight. 1N Hydrochloric acid was added to the reaction mixture and the mixture was subjected to extraction with ether. The ether was distilled off, and the resultant crude product was washed with hexane.

Workup

  1. customwas formed
  2. temperaturewas not refluxed
  3. stirringthe mixture was stirred at room temperature overnight
  4. extractionthe mixture was subjected to extraction with ether
  5. distillationThe ether was distilled off
  6. washthe resultant crude product was washed with hexane

Sources & evidence

ORD record
ord-95f956f28f4542d8a85303f623244133
Source dataset
uspto-grants-2000_01
Patent number
US06018070

Reaction notes

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