Trifluoroacetic acid → HCID 86657444, compound

HRID 2096558Notes

Reaction equation

HRID 2096558 reaction equation
[C:1]([CH:5]1CC[CH:8]([OH:11])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].N([O-])=O.[Na+].F[C:17](F)(F)[C:18]([OH:20])=[O:19]>>[C:1]([CH:5]([CH2:6][CH2:7][CH2:8][OH:11])[CH2:17][C:18]([OH:20])=[O:19])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 73914-tert-ButylcyclohexanolHCID 23668193Sodium Nitrite

Product 1

HCID 86657444HCID 86657444, compoundYield 41%

Procedure

4-tert-butylcyclohexanol (10 g, 64.1 mmol) was dissolved in trifluoroacetic acid and then NaNO2 (17.09 g, 256.4 mmol) was added to the solution at 0° C. under an air. After the resulting solution was stirred at room temperature for 5 hours, the solvent was removed in vacuo at room temperature and the residue was added into an aqueous 5% NaHCO3. After the solution was treated with methylene chloride, the aqueous solution was acidified with 10% HCl solution followed by extraction with ethyl acetate to give 3-tert-butyl-6-hydroxyhexanoic acid (5.26 g, 41%).

Workup

  1. customthe solvent was removed in vacuo at room temperature
  2. additionthe residue was added into an aqueous 5% NaHCO3
  3. additionAfter the solution was treated with methylene chloride
  4. extractionfollowed by extraction with ethyl acetate

Sources & evidence

ORD record
ord-f22ed53f72f94be9b47a026808d276da
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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