Tetrahydrofuran → Benzyl 3-chloro-5-hydroxybenzoate

HRID 1698984Notes

Reaction equation

HRID 1698984 reaction equation
[F-].O1CCCC1.[Cl:7][C:8]1[CH:9]=[C:10]([CH:21]=[C:22]([O:24][Si](C(C)(C)C)(C)C)[CH:23]=1)[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]>>[Cl:7][C:8]1[CH:9]=[C:10]([CH:21]=[C:22]([OH:24])[CH:23]=1)[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 28179Fluoride IonHCID 18322201Benzyl 3-chloro-5-(tert-butyldimethylsilyloxy)benzoate

Product 1

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

Procedure

A 1.0 M solution oftetrabutylammonium fluoride in tetrahydrofuran (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 methylcne chloride, the solution washed with dilute aqueous NaHCO3, dried over Na2SO4, 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 methylcne chloride
  3. washthe solution washed with dilute aqueous NaHCO3
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. washThe evaporated filtrate was then washed repeatedly with hexanes
  7. customdried in vacuo

Sources & evidence

ORD record
ord-96108f24f7604991b234da5ee3578713
Source dataset
uspto-grants-2002_02
Patent number
US06344486B1

Reaction notes

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