Sulfuric Acid → HCID 136346363, compound

HRID 1944210Notes

Reaction equation

HRID 1944210 reaction equation
O[C:2]([CH3:14])([CH3:13])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:11][CH3:12])=[C:8]([OH:10])[CH:9]=1.[C:15](#[N:17])[CH3:16].S(=O)(=O)(O)O.[Na]>C(O)(=O)C>[CH3:12][O:11][C:7]1[CH:6]=[C:5]2[C:4]([CH2:3][C:2]([CH3:14])([CH3:13])[N:17]=[C:15]2[CH3:16])=[CH:9][C:8]=1[OH:10]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 5360545SodiumHCID 68496261HCID 68496261, compound

Product 1

HCID 136346363HCID 136346363, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a flask (ice cooled) containing acetic acid (1.2 ml) was added 5-(2-hydroxy-2-methylpropyl)-2-methoxyphenol (500 mg, 2.5 mmol) and acetonitrile (0.27 ml, 5.1 mmol). To this was added sulfuric acid (1.2 ml) slowly with stirring. The reaction mixture was allowed to warm to rt and stirred for 4 h. The reaction mixture was poured onto ice-water and the aqueous solution neutralised with sodium C(Ar)bonate, then extracted with diethyl ether (2×) and ethyl acetate (2×) after saturation with sodium chloride. Purification (flashmaster: 20 g, 100% DCM to 100% EtOAc, then 30% MeOH/70% EtOAc) afforded the title compound (324 mg, 56%) as a pale brown solid. mp=160° C. dec. 1H NMR (270 MHz; CDCl3) 1.18 (6H, s, 2×CH3), 2.28 (3H, s, CH3), 2.59 (2H, s, CH2), 3.91 (3H, s, OCH3), 6.60 (1H, s, CH), 7.07 (1H, s, CH). 13C NMR (67.5 MHz; CDCl3) 23.21 (CH3), 28.02 (2×CH3), 38.81 (CH2), 53.78 (C(CH3)2), 55.98 (CH3), 110.47 (CH), 112.35 (CH)<121.96 (C), 128.86 (C), 144.35 (C), 148.88 (C), 161.39 (C N). LC/MS (ES+) tr=1.2 min, m/z 219.95 (M++H).

Workup

  1. temperatureTo a flask (ice cooled)
  2. stirringstirred for 4 h
  3. additionThe reaction mixture was poured onto ice-water
  4. extractionextracted with diethyl ether (2×) and ethyl acetate (2×) after saturation with sodium chloride
  5. customPurification (flashmaster

Sources & evidence

ORD record
ord-07515770c8614da1a62845daf10438f3
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

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