Resorcinol → 1-(2,4-Dihydroxyphenyl)-2-methylpropan-1-one

HRID 2355259Notes

Reaction equation

HRID 2355259 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].B(F)(F)F.CCOCC.[C:18](Cl)(=[O:22])[CH:19]([CH3:21])[CH3:20]>>[OH:2][C:1]1[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][C:8]=1[C:18](=[O:22])[CH:19]([CH3:21])[CH3:20]

Participants

4

Reactant 3

HCID 5054ResorcinolHCID 8000Boron trifluoride etherateHCID 62325Isobutyryl chloride

Product 1

HCID 159157311-(2,4-Dihydroxyphenyl)-2-methylpropan-1-oneYield 108.5%

Procedure

Combine resorcinol (1010 g, 9.17 mol) in boron trifluoride etherate (1.9 L, 15.0 mol) and mechanically stir in a 12-L Morton flask at room temperature. Treat mixture with isobutyryl chloride (880 mL, 8.37 mol), neat, over a 3 hour period via addition funnel, then stir overnight at room temperature. Pour the cooled oil into ˜10 kg of cracked ice and extract twice with ethyl ether (5 L total). Wash organic layers with water, saturated sodium chloride solution, dry with magnesium sulfate, filter, and evaporate filtrate to provide the title compound (1636 g, quantitative yield) as a reddish oil. HPLC Rt=4.29 min; 1H NMR (CDCl3) δ 13.03 (s, 1H), 7.69 (d, J=12.0 Hz, 1H), 6.4 (m, 2H), 3.51 (hept, J=8.0 Hz, 1H), 1.23 (d, J=8.0 Hz, 6H).

Workup

  1. additionneat, over a 3 hour period via addition funnel
  2. extractionextract twice with ethyl ether (5 L total)
  3. dry with materialWash organic layers with water, saturated sodium chloride solution, dry with magnesium sulfate
  4. filtrationfilter
  5. customevaporate filtrate

Sources & evidence

ORD record
ord-78eb6ef7cdde432b817a98584bbc058b
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

Loading…