Condensation of tertiary aliphatic alcohols with aromatic compounds in the presence of aluminum chloride. IV. Tertiary dimethylamylcarbinols with phenol was written by Huston, R. C.;Guile, R. L.. And the article was included in Journal of the American Chemical Society in 1939.SDS of cas: 35065-86-2 This article mentions the following:
The Grignard reagent from 2-methyl-3-bromobutane with AcCl gives 9.3% of 3,4-dimethylpentan-2-one, b744 135-40°; with MeI this yields 58% of 2,3,4-trimethylpentan-2-ol, b752 155-7°, nD13 1.4400, d2020 0.8095, γ20 27.48 dynes. Condensations were carried out by adding dropwise (2 h.) 32 g. of the alc. and 28 g. PhOH in 100 cc. petr. ether to 17 g. AlCl3 in petr. ether at 25-30° and after standing overnight decomposing with dilute HCl. The following compounds were thus prepared: 2-methyl-2-p-hydroxyphenylheptane (I), b2 114-17°, b741 293.5°, d2020 0.95053, nD16 1.5102, γ28 32.31, 69.5% yield; 2,3-dimethyl-2-p-hydroxyphenylhexane (II), b2 111-14°, b741 293°, d. 0.96836, n 1.5191, γ 33.74, 35.5%; 2,4-di-Me isomer (III), b2 113-16°, b741 290.5°, d. 0.95427, n 1.5121, γ 32.00, 58.5%; 2,5-di-Me isomer (IV), b2 105-7°, b741 288°, d. 0.95183, n 1.5110, γ 31.69, 64.6%; 2-methyl-3-ethyl-2-p-hydroxyphenylpentane (V), b2 109-11°, b741 293°, d. 0.96845, n 1.5190, γ 33.80, 28.3%; 2,4,4-tri-Me isomer (VI), b741 289°, m. 83°, 64.6%; 2,3,4-tri-Me isomer (VII), m. 74°, 23.1% yield; 2,3,3-tri-Me isomer, b741 325° (decomposition), m. 160°, 2.1%. Bz esters; I m. 27-23° (?), II m. 54.2-5.2°, III m. 37-8°, IV m. 46-7°, V m. 69-70°, VI m. 73-4°, VII m. 47-8°. α-Naphthylurethanes: I m. 120-1°, II m. 105-5.5°, III m. 119.5-20.5°, IV m. 132.5-33.5°, V m. 109.5-10.5°, VI m. 102-3°, VII m. 114.5-15.5°. p-Nitro- and p-amino-tert-octylbenzenes were prepared in establishing the structures of I-VI; 2-methyl-2-p-nitrophenylheptane, b2 148-50°; p-NH2 derivative, b2 108-11°; 2,3-dimethyl-2-p-nitrophenylhexane, b2 133-5°; 2,4-di-Me isomer, b2 135-7°; 2,5-di-Me isomer, b2 129-31°; the corresponding p-NH2 derivatives b4 115-19°, b2 99-101° and b2 99-102°; 2-methyl-3-ethyl-2-p-nitrophenylpentane, b4 127-30°; 2,4,-4-tri-Me isomer, b4 108-10°; the corresponding p-NH2 derivatives b2 103-6° and b5 112-15°. In the experiment, the researchers used many compounds, for example, 3-Bromophenyl acetate (cas: 35065-86-2SDS of cas: 35065-86-2).
3-Bromophenyl acetate (cas: 35065-86-2) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.SDS of cas: 35065-86-2
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary