Tetrabutylammonium Fluoride → Benzyl 3-chloro-5-hydroxybenzoate

HRID 1698858Notes

Reaction equation

HRID 1698858 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:19][C:20]1[CH:21]=[C:22]([CH:33]=[C:34]([O:36][Si](C(C)(C)C)(C)C)[CH:35]=1)[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>>[Cl:19][C:20]1[CH:21]=[C:22]([CH:33]=[C:34]([OH:36])[CH:35]=1)[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 18322201Benzyl 3-chloro-5-(tert-butyldimethylsilyloxy)benzoate

Product 1

HCID 18322181Benzyl 3-chloro-5-hydroxybenzoateYield 98%

Procedure

A 1.0 M solution of tetrabutylammonium fluoride in tetrahydrofuiran (26.6 mL, 26.6 mmol) was added to neat benzyl ester 24 (5.00 g, 13.3 mmol), the reaction stirred 10 minutes at ambient temperature, and evaporated in vacuo. The crude product was dissolved in methylene chloride, the solution washed with dilute aqueous NaHCO3, dried overNa2SO4, and filtered. The evaporated filtrate was then washed repeatedly with hexanes and dried in vacuo giving product 25 as a gold oil (3.40 g, 98%). 1H NMR (300 MHz, CDCl3) δ 7.35 (m, 7H), 7.1 (t, 1H, J=2.1 Hz), 5.28 (s, 2H).

Workup

  1. customevaporated in vacuo
  2. dissolutionThe crude product was dissolved in methylene chloride
  3. washthe solution washed with dilute aqueous NaHCO3
  4. customdried overNa2SO4, and
  5. filtrationfiltered
  6. washThe evaporated filtrate was then washed repeatedly with hexanes
  7. customdried in vacuo

Sources & evidence

ORD record
ord-43ba92063311405bb4b8687f541be0ac
Source dataset
uspto-grants-2002_02
Patent number
US06344466B2

Reaction notes

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