Hydrochloric Acid → 4-Decanoyloxy-2-fluorobenzoic acid

HRID 247803Notes

Reaction equation

HRID 247803 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:22])[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>[F:1][C:2]1[CH:10]=[C:9]([O:11][C:12](=[O:22])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 218852-DimethylaminopyridineHCID 66982Decanoyl chlorideHCID 27833982-Fluoro-4-hydroxybenzoic Acid

Product 1

HCID 193652624-Decanoyloxy-2-fluorobenzoic acidYield 70.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-fluoro-4-hydroxybenzoic acid (2 g) and triethylamine (1.4 g) in dichloromethane (40 ml) were added decanoylchloride (2.7 g) and dimethylaminopyridine (0.2 g). The solution was stirred at room temperature for about 20 hours. To the solution was added dilute aqueous hydrochloric acid solution and the organic layer was separated by a funnel. The layer was distilled to remove the solvent. The residue was washed with n-hexane and dried to obtain the titled compound (about 2.8 g).

Workup

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

Sources & evidence

ORD record
ord-6ceb8d92d3fa42cb988da818a488af00
Source dataset
uspto-grants-1993_05
Patent number
US05207947

Reaction notes

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