4-Hydroxybenzoic Acid → 4-Undecanoyloxybenzoic acid

HRID 247789Notes

Reaction equation

HRID 247789 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:11](Cl)(=[O:22])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].CN(C1C=CC=CN=1)C.Cl>ClCCl.C(N(CC)CC)C>[C:11]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)(=[O:22])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

7

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 218852-DimethylaminopyridineHCID 87287Undecanoyl chloride

Product 1

HCID 154568744-Undecanoyloxybenzoic acidYield 75.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of p-hydroxybenzoic acid (3 g) and triethylamine (2.4 g) in dichloromethane (30 ml) were added undecanoyl chloride (4.5 g) and dimethylaminopyridine (0.2 g). The mixture was stirred at room temperature for about 20 hours. After dilute aqueous hydrochloric acid solution was added, an organic layer was separated by a funnel. After the solution was distilled to remove the solvent, the residue was washed with n-hexane and dried to obtain the titled compound (about 5 g).

Workup

  1. customan organic layer was separated by a funnel
  2. distillationAfter the solution was distilled
  3. customto remove the solvent
  4. washthe residue was washed with n-hexane
  5. customdried

Sources & evidence

ORD record
ord-95f5ab90248642f89e9fa8c60e1b1a59
Source dataset
uspto-grants-1993_05
Patent number
US05207947

Reaction notes

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