Sodium Hydroxide → HCID 66784650, compound

HRID 1095433Notes

Reaction equation

HRID 1095433 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1)=[O:15].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>CO>[OH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:23])([F:24])[F:25])=[CH:18][CH:17]=1)=[O:15]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 59799436HCID 59799436, compound

Product 1

HCID 66784650HCID 66784650, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a magnetically stirred solution of 7-(tetrahydropyran-2-yloxy)-1-[4-(trifluoromethyl)phenyl]heptan-1-one (7.70 g, 0.0215 mol) in methanol (50 ml) was added para-toluenesulfonic acid hydrate (4.18 g, 0.022 mol). The resulting acidic mixture (pH˜2, pH paper) was reacted at room temperature for 20 hours. NaOH (1N) was added until the solution was neutral (pH˜7, pH paper) and the resulting mixture was concentrated in vacuo. NaOH (1N, 50 ml) was added and the mixture was extracted with dichloromethane (3×). The combined organic layers were successively washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to give crude 7-hydroxy-1-[4-(trifluoromethyl)phenyl]heptan-1-one (5.85 g, 99% yield) as a white solid. This obtained solid was treated with pyridine (29.6 ml) and a solution of tosyl chloride (17.72 g, 0.093 mol) in pyridine (89 ml) was added at 0° C. The mixture was allowed to attain room temperature and reacted for 1 hour. The mixture was cooled at −10° C. and quenched with excess water. Extraction with diethyl ether (3×), followed by drying over Na2SO4, filtering and concentration in vacuo gave crude product which was purified by column chromatography (dichloromethane/heptane=2/1 (v/v)) to give pure toluene-4-sulfonic acid 7-oxo-7-[4-(trifluoromethyl)phenyl]heptyl ester (7.91 g, 87% yield). 1H-NMR (400 MHz, CDCl3) δ 1.35-1.38 (m, 4H), 1.57-1.73 (m, 4H), 2.44 (s, 3H), 2.97 (t, J=7, 2H), 4.03 (t, J=7, 2H), 7.35 (d, J˜8, 2H), 7.73 (d, J˜8, 2H), 7.79 (d, J˜8, 2H), 8.04 (d, J˜8, 2H).

Workup

  1. customThe resulting acidic mixture (pH˜2, pH paper) was reacted at room temperature for 20 hours
  2. concentrationthe resulting mixture was concentrated in vacuo
  3. additionNaOH (1N, 50 ml) was added
  4. extractionthe mixture was extracted with dichloromethane (3×)
  5. washThe combined organic layers were successively washed with water and brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2a76cd5dcb44d9eb49ee8416eb75b3d
Source dataset
uspto-grants-2012_03
Patent number
US08138174B2

Reaction notes

Loading…