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

HRID 247784

Reaction equation

HRID 247784 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 78.7%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of p-hydroxybenzoic acid (3 g) and triethylamine (2.4 g) in dichloromethane (30 ml) were added decanoyl chloride (4.3 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 to the mixture, 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-d0f29f1ace974ea1bd0bc63aa6f31766
Source dataset
uspto-grants-1993_05
Patent number
US05207947

Linked notes

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