1-Nonanol, 9-bromo- → 9-Bromononanoic Acid

HRID 332635Notes

Reaction equation

HRID 332635 reaction equation
[Cr](Cl)([O-])(=O)=[O:2].[NH+]1C=CC=CC=1.[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22]>C(Cl)Cl>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:2])=[O:22]

Participants

4

Reactant 2

HCID 1087001-Nonanol, 9-bromo-HCID 178418287HCID 178418287, compound

Product 1

HCID 5482219-Bromononanoic AcidYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium chlorochromate (38.7 g, 180 mmol) and silica 60A (39 g, particle size 35-70 micron) suspended in DCM (250 mL) were stirred at RT for 45 minutes. 9-Bromononanol (26.7 g, 120 mmol) was added, in one portion, and the suspension was stirred at RT for 18 hours. The reaction mixture was filtered through a celite plug, and the resulting filtrate concentrated under vacuum affording the title compound (28.0 g, >100%). The material was used without further purification in the next step.

Workup

  1. stirringthe suspension was stirred at RT for 18 hours
  2. filtrationThe reaction mixture was filtered through a celite plug
  3. concentrationthe resulting filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-78d30d7b1dbc4619a03bb08bd8af16e2
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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