Water → HCID 67019287, compound

HRID 1753994Notes

Reaction equation

HRID 1753994 reaction equation
[CH3:1][CH:2]([CH3:13])[CH2:3][CH2:4][CH:5]1[C:10](=[O:11])[CH2:9][CH2:8][CH2:7][C:6]1=[O:12].[CH2:14](O)[CH:15]([CH3:17])[CH3:16].O>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][CH:2]([CH3:13])[CH2:3][CH2:4][C:5]1[C:10](=[O:11])[CH2:9][CH2:8][CH2:7][C:6]=1[O:12][CH2:14][CH:15]([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 962WaterHCID 6560IsobutanolHCID 67019298HCID 67019298, compound

Product 1

HCID 67019287HCID 67019287, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

A solution of ketoenol 7 (68.0 g, 374 mmol), isobutanol (83.0 g, 1120 mmol), and p-toluenesulfonic acid (1.0 g, 1.2 mmol) in anhydrous benzene (730 mL) was refluxed overnight with azeotropic removal of water (Dean-Stark trap). The reaction mixture was cooled to room temperature, washed with saturated sodium bicarbonate solution (3×250 mL), brine (2×250 mL) and concentrated to give 88.0 g (98.9%) of 8 as a thick oil, which solidified upon cooling. MS m/z 239 (M+1); 1H NMR (300 MHz, CDCl3) δ 3.75 (d, 2H), 2.5 (t, 2H), 2.3-2.2 (m, 4H), 2.0-1.9 (m, 3H), 1.6-1.5 (m, 1H), 1.2-1.1 (m, 2H), 1.0 (d, 6H), 0.9 (d, 6H); 13C NMR (CDCl3) δ 198.4, 171.5, 120.1, 73.9, 38.0, 36.5, 28.8, 28.4, 25.5, 22.6, 21.1, 20.1, 19.1.

Workup

  1. washwashed with saturated sodium bicarbonate solution (3×250 mL), brine (2×250 mL)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-b82880bada3e4a38af89b84e46dbd486
Source dataset
uspto-grants-2015_10
Patent number
US09169190B2

Reaction notes

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