Sulfuric Acid → HCID 66969973, compound

HRID 1360325Notes

Reaction equation

HRID 1360325 reaction equation
[OH:1]S(O)(=O)=O.CC1(C)C[O:10][C:9]([C:12]2[C:20]([CH2:21][CH3:22])=[CH:19][C:18]([O:23][CH3:24])=[CH:17][C:13]=2[C:14]([OH:16])=[O:15])=N1>O1CCOCC1>[CH2:21]([C:20]1[CH:19]=[C:18]([O:23][CH3:24])[CH:17]=[C:13]([C:14]([OH:16])=[O:15])[C:12]=1[C:9]([OH:10])=[O:1])[CH3:22]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 66970103HCID 66970103, compound

Product 1

HCID 66969973HCID 66969973, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

A solution of 6.00 mol/L H2SO4 (aq.) (700 mL) was added to a solution of compound G (65.7 g, 237 mmol) in 1,4-dioxane (700 mL) at room temperature. The mixture was heated at 130° C. (oil bath temperature) and stirred. After 64 h the mixture was concentrated in vacuo, and cooled to 0° C. The precipitate was filtered and rinsed with a small amount of water to give the desired compound H (23.8 g, 106 mmol) as an off-white solid. The filtrate was extracted twice with ethyl acetate and the combined organic phases were dried over Na2SO4, filtered, and concentrated in vacuo to give the desired compound H (10.8 g, 48.2 mmol) as an off-white solid. The aqueous phase (after salting with NaCl) was extracted with CHCl3/MeOH (4/1), and the combined organic phases were dried over Na2SO4 and concentrated in vacuo to recover the starting material G (26%). 1H NMR (DMSO-d6 400 MHz): δ 1.14 (3H, t, J=7.6 Hz), 2.60 (2H, q, J=7.6 Hz), 3.80 (3H, s), 7.04 (1H, d, J=2.4 Hz), 7.16 (1H, d, J=2.4 Hz). EIMS (+): 224 [M]+

Workup

  1. concentrationAfter 64 h the mixture was concentrated in vacuo
  2. temperaturecooled to 0° C
  3. filtrationThe precipitate was filtered
  4. washrinsed with a small amount of water

Sources & evidence

ORD record
ord-f0959b9f71e449a4b477e28e5965f51a
Source dataset
uspto-grants-2011_02
Patent number
US07879846B2

Reaction notes

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