Hydrochloric Acid → 5169-81-3

HRID 2229833Notes

Reaction equation

HRID 2229833 reaction equation
[CH3:1][C:2]1[O:11][C:10](=[O:12])[C:9]2[C:8](=[O:13])[CH2:7][CH:6]([CH:14]([CH3:16])[CH3:15])[O:5][C:4]=2[CH:3]=1.[OH-].[K+].C(OC)(C)(C)C.Cl>CO>[OH:5][C:4]1[CH:3]=[C:2]([CH3:1])[O:11][C:10](=[O:12])[C:9]=1[C:8](=[O:13])[CH:7]=[CH:6][CH:14]([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 15413tert-Butyl methyl etherHCID 10125188HCID 10125188, compound

Product 1

HCID 1362314175169-81-3Yield 58.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 10 ml of methanol, 222 mg of 2, 3-dihydro-7-methyl-2-(1-methylethyl)-4H, 5H-pyrano[4,3-b]pyran-4,5-dione were dissolved, and 200 mg of potassium hydroxide were added thereto and stirred at room temperature for 1 hour. After that, methyl t-butyl ether and 3% hydrochloric acid were added to the reaction mixture. The separated organic layer was washed with saturated brine once, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 130 mg of 4-hydroxy-6-methyl-3-(4-methyl-2-pentenoyl)-2-pyrone. 1H-NMR (CDC13, TMS) δ (ppm): 1.13 (6H, d), 2.27 (3H, s), 2.60 (1 H, m), 5.93 (1H, s), 7.23 (1H, dd), 7.58 (1H, d).

Workup

  1. washThe separated organic layer was washed with saturated brine once
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e1dce4e219694670b3a075c9b4d7ccda
Source dataset
uspto-grants-2002_07
Patent number
US06420569B1

Reaction notes

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