4-Hydroxybenzoic Acid → Benzoic acid, 4-((1-oxodecyl)oxy)-

HRID 1585437Notes

Reaction equation

HRID 1585437 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:28])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].Cl>ClCCl.CN(C1C=CC=CN=1)C>[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:28])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

7

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 66982Decanoyl chloride

Product 1

HCID 3608562Benzoic acid, 4-((1-oxodecyl)oxy)-Yield 87.2%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

13.8 Grams (0.1 mol) of 4-hydroxybenzoic acid was dissolved in 140 ml of dichloromethane. To this mixture were consecutively added 16 ml of triethylamine, 20.1 g (0.11 mol) of n-decanoic acid chloride and 0.97 g (0.0079 mol) dimethylaminopyridine, and the mixture was stirred at room temperature over 1 day and night. To this reaction mixture was added 50 ml of 10% hydrochloric acid, and the mixture was extracted with 100 ml of ether three times. An organic layer was washed with 100 ml of sodium chloride aqueous solution three times, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was washed with 400 ml of hexane to give 25.5 g (yield 82%) of 4-decanoyloxybenzoic acid as an end product.

Workup

  1. extractionthe mixture was extracted with 100 ml of ether three times
  2. washAn organic layer was washed with 100 ml of sodium chloride aqueous solution three times
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. washthe residue was washed with 400 ml of hexane

Sources & evidence

ORD record
ord-4418f7a4f32447fa91280b5adca9106c
Source dataset
uspto-grants-1999_08
Patent number
US05938973

Reaction notes

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