Hydrochloric Acid → 2-Fluoro-4-n-tridecanoyloxybenzoic acid

HRID 247804

Reaction equation

HRID 247804 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](Cl)(=[O:25])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].CN(C1C=CC=CN=1)C.Cl>ClCCl.C(N(CC)CC)C>[F:1][C:2]1[CH:10]=[C:9]([O:11][C:12](=[O:25])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 218852-DimethylaminopyridineHCID 87288Tridecanoyl chlorideHCID 27833982-Fluoro-4-hydroxybenzoic Acid

Product 1

HCID 193652682-Fluoro-4-n-tridecanoyloxybenzoic acidYield 59.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-fluoro-4-hydroxybenzoic acid (1.4 g) and triethylamine (1.0 g) in dichloromethane (40 ml) were added tridecanoyl chloride (2.0 g) and dimethylaminopyridine (0.2 g). The solution was stirred at room temperature for about 20 hours and thereto was added dilute aqueous hydrochloric acid solution. The organic layer was separated by a funnel and distilled to remove the solvent. The residue was washed with n-hexane and dried to obtain the titled compound (about 1.8 g).

Workup

  1. customThe organic layer was separated by a funnel
  2. distillationdistilled
  3. customto remove the solvent
  4. washThe residue was washed with n-hexane
  5. customdried

Sources & evidence

ORD record
ord-01c87d2080664374a114683782c76fb9
Source dataset
uspto-grants-1993_05
Patent number
US05207947

Linked notes

Loading…