Hydrochloric Acid → HCID 14424136, compound

HRID 1762355Notes

Reaction equation

HRID 1762355 reaction equation
OC[CH2:3][C:4]1[C:9]([OH:10])=[C:8]([O:11][CH3:12])[C:7]([O:13][CH3:14])=[C:6](O)[C:5]=1C.[H-].[Na+].[CH3:19]I.Cl.[CH2:22]([CH2:25][O:26][CH3:27])[O:23][CH3:24]>>[CH3:24][O:23][C:22]1[C:5]([CH2:6][CH2:7][O:13][CH3:14])=[C:4]([CH3:3])[C:9]([O:10][CH3:19])=[C:8]([O:11][CH3:12])[C:25]=1[O:26][CH3:27]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 80711,2-Dimethoxyethane2×HCID 24758Sodium hydrideHCID 14424135HCID 14424135, compound

Product 1

HCID 14424136HCID 14424136, compound

Procedure

6-(2-Hydroxyethyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (350 mg) which was obtained in Example 3 was treated with sodium hydrosulfite to give 6-(2-hydroxyethyl)-2,3-dimethoxy-5-methylhydroquinone (313 mg). A solution of the hydroquinone (290 mg) in dimethoxyethane (DME, 4 ml) was added dropwise to a suspension of 60% sodium hydride (450 mg) and methyl iodide (2.7 ml) in DME (3 ml) within 90 minutes at 45°-60° C. After cooling, the reaction mixture was treated with diluted hydrochloric acid. The aqueous layer was separated and extracted with ethyl ether. The combined ethereal layer was worked up in the usual manner. The resulting residue (240 mg) was purified by a silica gel column chromatography to give 1,2,3,4-tetramethoxy-5-methyl-6-(2-methoxyethyl)benzene (330 mg). To a solution of this compound (210 mg) in tetrahydrofuran (14 ml), silver (II) oxide (490 mg) and 6N nitric acid (1 ml) were added. After being stirred for 5 minutes at 0° C., silver (II) oxide (2 g) and 6N nitric acid (2 ml) were further added. The reaction mixture was worked up in the usual manner and purified by column chromatography to give 2,3-dimethoxy-5-methyl-6-(2-methoxyethyl)-1,4-benzoquinone as an orange oil. NMR spectrum (δ value in CDCl3): 2.05 (3H, s, CH3 on ring), 2.73 (2H, t, J=6 Hz, CH2 on ring), 3.32 (3H, s, OCH3), 3.47 (2H, t, J=6 Hz, CH2O), 4.00 (6H, s, OCH3 on ring).

Workup

  1. temperatureAfter cooling
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl ether
  4. customThe resulting residue (240 mg) was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-78a80759b7c04594b0cafc9b52dd2c6d
Source dataset
uspto-grants-1989_05
Patent number
US04831265

Reaction notes

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