Winstein, S. published the artcileThe role of neighboring groups in replacement reactions. XVIII. Migration of the methoxyl group, Safety of 2-Methyl-3-bromo-2-butanol, the publication is Journal of the American Chemical Society (1952), 1160-4, database is CAplus.
cf. C.A. 45, 4661f. A result of participation of a functional neighboring group in a replacement process is migration of the neighboring group. Such a migration of a MeO group occurs in the solvolysis of Me2C(OMe)CHBrMe (I), which solvolyzes to give Me2C(OH)CH(OMe)Me (II). EtMe2COH with H2SO4 yielded Me2C:CHMe (III), b752 38.7-8.9°, nD25 1.3845. III (175 cc.) added dropwise to 224 g. N-bromosuccinimide (IV) in 2 1. MeOH, the mixture let stand overnight, added to 2 1. saturated NaCl, and the oil extracted with Et2O yielded 227 g. I, b40 69-9.5°, nD25 1.4533, d25 1.2632. MRD is given for the compounds prepared Me2CHCH(OH)Me, b760 111.8-11.9°, and 6.9 g. Na refluxed in 250 cc. petr. ether (b. 150-90°), the solution treated with 42.5 g. MeI and refluxed 1 h. yielded 13.9 g. 3-methoxy-2-methylbutane, b760 83-3.5°, nD20 1.3838, nD25 1.3812, d25 0.7542. I (36.2 g.), 250 cc. MeOH, 10 g. Pd-CaCO3, and 17 g. KOH shaken 24 h. with H at 1 atm., the solution filtered, added to 250 cc. water, and extracted with petr. ether yielded 10.6 g. Me2C(OMe)Et, b760 85-6.5°, nD20 1.3885. III (230 cc.) added dropwise during 20 min. to 270 g. IV in 21. water, the mixture stirred 1 h., and extracted the next day with Et2O, yielded 81.1 g. 2,3-epoxy-2-methylbutane (V), b760 73-3.3°, nD25 1.3822, d25 0.8000. MeCH(OMe)CO2Me, b747 129-30°, nD25 1.3957, d25 0.9948, (0.45 mol) with 1 mol Me Grignard reagent yielded 21.8 g. II, b752 129.5-30°, nD25 1.4100, d25 0.8877; V with Na yielded 53% II. V (33.2 g.) in 155 cc. MeOH treated with 2 drops H2SO4 yielded 34.6 g. 3-methyl-3-methoxy-2-butanol (VI), b760 143-4°, nD25 1.4193, 0.9151. I (90.5 g.), 30 g. CaCO3, and 400 cc. water treated dropwise during 20 min. with 95 g. AgNO3, the mixture stirred 4 h. and extracted with Et2O yielded 35.3 g. II, and 6.4 g. Me2CHCOMe, b760 92-5° (2,4-dinitrophenylhydrazone, m. 122-2.5°); VI gave 80% recovered alc., b760 141-4°, and II gave 80.6% recovered alc., b760 129-30°. I (90.5 g.), 92 g. AgNO3, and 500 cc. AcOH stirred 1 h. at 90-110°, the mixture filtered, and the filtrate neutralized with 6N KOH under Et2O yielded 16.8 g. II, b752 129.5-30°. VI (20 g.), 20 g. Ac2O, and 50 cc. pyridine refluxed 1 h. yielded 22 g. acetate, b50 85°, nD25 1.4122, d25 0.9456. VI (32.1 g.) and 6.25 g. Na dissolved in 250 cc. refluxing petr. ether (b. 230-60°) and the solution treated with 39 g. MeI in 100 cc. Et2O and refluxed 30 min. yielded 17.3 g. 2,3-dimethoxy-2-methylbutane (VII), b760 125-5.5°, nD25 1.4026, d25 0.8571. I (95.5 g.) in 500 cc. MeOH refluxed 2 h. with 70 g. Ag2O yielded 44.8 g. VII, b760 125-6°, nD25 1.4018. III (53 cc.), 89 g. IV, and 1.5 1. water stirred 1.5 h. in an ice bath, the mixture saturated with NaCl, and extracted with Et2O, yielded 67.33 g. trimethylethylene bromohydrin (Me2C(OH)CHBrMe) (VIII), b10 48-51°, nD25 1.4712. AgNO3 (9.35 g.) in 200 cc. water added dropwise to 88.5 g. VIII and 84 g. NaHCO3 in 300 cc. water during 1 h., the mixture stirred 1 h., extracted with Et2O, the Et2O partially distilled, the residue shaken with 42 g. NaHCO3 and 47 g. AgNO3 in 200 cc. water extracted with Et2O, and the extract distilled, yielded 21.90 g. V, b760 72-3°, nD25 1.3826, and 1.95 g. Me2CHCOMe, b769 90-6° (2,4-dinitrophenylhydrazone, m. 122-2.5°).
Journal of the American Chemical Society published new progress about 2588-77-4. 2588-77-4 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic Chain, name is 2-Methyl-3-bromo-2-butanol, and the molecular formula is C10H15BO4, Safety of 2-Methyl-3-bromo-2-butanol.
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