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CAS No. : | 504-15-4 | MDL No. : | MFCD00002291 |
Formula : | C7H8O2 | Boiling Point : | - |
Linear Structure Formula : | C6H3(CH3)(OH)2 | InChI Key : | OIPPWFOQEKKFEE-UHFFFAOYSA-N |
M.W : | 124.14 | Pubchem ID : | 10436 |
Synonyms : |
3,5-Dihydroxytoluene;5-Methylresorcinol;NSC 12441
|
Chemical Name : | 5-Methylbenzene-1,3-diol |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With sodium hydrogencarbonate; In dichloromethane; water; at 20℃; for 48h; | a) 5-Methyl-3-(3-pyridinylsulfoxy)phenol A mixture of orcinol monohydrate (1.42 g, 0.01 mol) and 3-pyridylsulfonyl chloride hydrochloride (2.13 g, 0.01 mol), as prepared in J. Am. Chem. Soc., 114:4889 (1992), in saturated aqueous sodium bicarbonate (17.5 mL) and dichloromethane (50 mL) was stirred rapidly at ambient temperature for 2 days. The dichloromethane was separated and the aqueous layer was extracted with ethyl acetate (3 x 25 mL). The ethyl acetate and dichloromethane extracts were combined and washed with brine, dried over anhydrous sodium sulfate, and evaporated to dryness. The residue was recrystallized from ether and hexane, collected by filtration, and dried under high vacuum to give 1.54 g of a white solid (58percent yield). 1H-NMR (300 MHz, CDCl3) delta 9.03 (d, 1 H), 8.88 (dd, 1 H), 8.16 (dt, 1 H), 7.5 (m, 1 H), 6.57 (d, 1 H), 6.42 (s, 1 H), 6.32 (t, 1 H), 2.24 (s, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 2 1,2-Dihydro-9-hydroxy-7-methyl-4-oxo-4H-thieno[2,3-c] [1]benzopyran Following a procedure similar to that described in Example 1B hereinabove, methyl 3-oxo-2,3,4,5-tetrahydrothiophene-2-carboxylate is reacted with 5-methylresorcinol to give 1,2-dihydro-9-hydroxy-7-methyl-4-oxo-4H-thieno[2,3-c] [1]benzopyran. | ||
EXAMPLE 91 1,2-Dihydro-9-hydroxy-7-methyl-4-oxo-4H-thieno[2,3-c][1]benzopyran Following the procedure similar to that described in Example 1B hereinabove, methyl 3-oxo-2,3,4,5-tetrahydrothiophene-2-carboxylate is reacted with 5-methylresorcinol to give 1,2-dihydro-9-hydroxy-7-methyl-4-oxo-4H-thieno[2,3-c][1]benzopyran. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With sodium carbonate; In water; at 25.0℃; for 2.0h; | General procedure: Imidazo[1,2-a]pyrimidine-2-carbaldehyde [40] (100 mg,0.68 mmol, 1.0 equiv.), 58 mg malononitrile (0.88 mmol, 1.3equiv.), and enolizable compounds (0.88 mmol, 1.3 equiv.)were dissolved in 5 cm3water or a mixture of water:ethylalcohol (4:1). Sodium carbonate (0.88 mmol, 93 mg, 1.3equiv.) in 2 cm3water was added and the mixture was stirredat room temperature for various times (2-7 h). The reactionprocess was monitored with thin layer chromatographyusing different ratio of hexane:ethyl acetate mixture assolvent. After completion of the reaction, the mixture waspoured into brine solution and stirred for 15 min. The resultingsolid was suction filtered using filter paper with smallpore size and washed with water. The pure products 4a-4gwere obtained by crystallization or washing with varioussolvents. Products were stored under argon atmosphere toprevent decomposition. |