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

HRID 247802

Reaction equation

HRID 247802 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:21])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].CN(C1C=CC=CN=1)C.Cl>C(Cl)Cl.O.C(N(CC)CC)C>[CH2:12]([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:21])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

8

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 218852-DimethylaminopyridineHCID 66982Decanoyl chloride

Product 1

HCID 3608562Benzoic acid, 4-((1-oxodecyl)oxy)-Yield 42.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 4-hydroxybenzoic acid (3 g), decanoic acid chloride (4.3 g), triethylamine (2.4 g) and dimethylaminopyridine (0.2 g) in methylene chloride (50 ml) was stirred at room temperature for 24 hours, and then poured in water. The solution was neutralized with dilute aqueous hydrochloric acid solution and extracted with dimethyl ether. The extracted product was dried over anhydrous magnesium sulfate and distilled to remove the solvent. The residue was washed enough with hexane to obtain the titled compound (2.7 g).

Workup

  1. extractionextracted with dimethyl ether
  2. dry with materialThe extracted product was dried over anhydrous magnesium sulfate
  3. distillationdistilled
  4. customto remove the solvent
  5. washThe residue was washed enough with hexane

Sources & evidence

ORD record
ord-081baeb5b5c44533a76afd5b27c1e8e0
Source dataset
uspto-grants-1993_05
Patent number
US05207947

Linked notes

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