4- Hydroxy-2-methylbenzaldehyde

The male-produced sex pheromone that functions to attract females in Acarus immobilis is composed of a mixture (active at 100-1000 ng) of the male-specific hydrocarbons pentadecane (71), heptadecane (76), (Z)-8-heptadecene (77), and (Z,Z)-6,9-heptadecadiene (78), plus several other hydrocarbons (tridecane (65), pentacosane (86), heptacosane (87), and nonacosane (88)) present in extracts from both sexes. The female-produced sex pheromone that functions as a courtship-stimulating pheromone for males consists of 2-hydroxy-6-methylbenzaldehyde... 

Ryono, A., Mori, N., Okabe, K. and Kuwahara, Y. (2001). Chemical ecology of astigmatid mites LVIII. 2-Hydroxy-6-methylbenzaldehyde sex pheromone of Cosmoglyphus hughesi (Acari Acaridae). Applied Entomology and Zoology 36 77-81. 

Hydroxy-6-methylbenzaldehyde the female sex pheromone of the house dust mite Dermatophagoides farinae (Astigmata Pyroglyphidae). Japanese Journal of Sanitary Zoology 52 269-277. 

Benzenediamine (352) and 4-p-chlorobenzyl-3-hydroxy-5-p-tolyl-2,5-dihy-dro-2-furanone (353) gave 3-(p-chlorophenethyl)-2(177)-quinoxahnone (354) with loss of p-methylbenzaldehyde (isolated as its phenyUiydrazone) (EtOH,... 

Unsymmetric compartmental ligands that allow for the controlled synthesis of unsymmetric Ni2 or heterobimetallic NiM complexes have received particular attention.1876,1892 A wide range of such ligands derived particularly from 2-hydroxy-3-hydroxymethyl-5-methylbenzaldehyde and 2-hydroxy-3-hydroxymethyl-bromo-benzaldehyde has now been prepared and used for Ni com-plexation. These ligands have monopodal iminic pendent arms and either mono- or dipodal aminic pendent arms and the terminal donors of the pendent arms can be provided by pyridine, imidazole, and tertiary amino groups.1893-1897 Complexes are usually prepared by reaction of the requisite Ni11 salts with the preformed ligand. 

To a solution of red phosphorus (3.1 g, 0.1 mol) in DMSO (6 ml) the following was added successively potassium hydroxide (0.95 g, 17 mmol) in water (50 mmol) and aldehyde, 4-methylbenzaldehyde (0.90 g, 7.5 mmol). The reaction mixture was sonicated for 10 min, after which it was filtered to remove excess phosphorus. The filtrate was then acidified to pH = 2-3 with 37% aqueous HC1 and extracted with chloroform. The aqueous portion was concentrated to dryness, and the residue dissolved in a minimum of acetic acid. The supernatant layer was separated from the solid and concentrated to dryness to give the product a-hydroxy-p-methylbenzylphosphonous acid in 30% yield. 

Biological. A proposed microbial degradation mechanism is as follows 4-hydroxy-3-methylbenzyl alcohol to 4-hydroxy-3-methylbenzaldehyde to 3-methyl-4-hydroxybenzoic acid to 4-hydroxyisophthalic acid to protocatechuic acid to p ketoadipic acid (Chapman, 1972). In anaerobic sludge, diethyl phthalate degraded as follows monoethyl phthalate to phthalic acid to protocatechuic acid followed by ring cleavage and mineralization (Shelton et al, 1984). 

Hydroxy-4-methylbenzaldehyde [57295-30-4] m 116-117 , b 179 /15mm. Crystd from water. 

Sodium hydride (97%), triethyl phosphite (99%), a,a dibromo-p-xylene (97%), 4-hydroxy-3-methylbenzaldehyde (97%), 3-ethoxy-4-hydroxybenzaldehyde (99%), vanillin (99%), and valeryl chloride (98%), were supplied by Aldrich Chemical Co. and were used without further purification 4-hydroxybenzaldehyde (96%, Aldrich) was resublimed prior to use. The add chlorides were supplied by Aldrich Chemical Co. and, with the exception of sebacoyl chloride (99+%), were fractionally distilled at reduced pressure through a 6-inch Vigreux column prior to use pimeloyl chloride 95-6°C at 1.1 torr, suberoyl 114-16°C at 2.2 torr, azelaoyl 104-6°C at 0.35 torr. Dibromoalkanes from Aldrich Chemical were fractionally distilled prior to use 1,7-dibromoheptane 111-114°C at 1.4 torr, 1,9-dibromononane 135-137°C at 2.7 torr, 1,11-dibromoundecane 129-131 °C at 0.85 torr. Tetrabutylammonium iodide (98%) was supplied by Aldrich. Reagent grade solvents were obtained from Fisher Scientific. 

Problem 19.23 Prepare (a) 2-bromo-4-hydroxytoluene from toluene, (b) 2-hydroxy-5-methylbenzaldehyde from p-toluidine, (c) m-methoxyaniline from benzenesulfonic acid. ... 

C8H8CIN04 1-chloro-2,4-dimethoxy-5-nitrobenzene 119-21-1 495.45 43.447 1.2 13424 C8H802 2-hydroxy-4-methylbenzaldehyde 698-27-1 496.15 43.514 1,2... 

C8H8CIN302 1-methyl-1-nitroso-3- p-chlorophenyl)urea 25355-61-7 310.15 25.990 1,2 13425 C8H802 2-hydroxy-5-methylbenzaldehyde 613-84-3 490.65 42.986 1,2... 

Benzaldehyde, 2-hydroxy-4-methyl- 2-hydroxy-4-methylbenzaldehyde 172a 174a, 174b... 

Hydroxy-4-methylbenzaldehyde [57295-30-4] M 136.1, m 73°, pKEst 10.2. Crystallise it from water or CeH6 (m 71-71°). The 0-methyl ether has m 45-46 (from Et20/hexane). [Sedgwick Allot J Chem Soc 2820 1923, Flitsch et al. Justus Liebigs Ann Chem 1413 1985, Beilstein 8 H 100,8II103,8IV 368.]... 

---