Maguet, Louis published the artcileEsterification of 3-methyl-1,3-butanediol, Category: esters-buliding-blocks, the publication is Bulletin de la Societe Chimique de France (1965), 3262-6, database is CAplus.
A method is described for the diesterification of Me2C(OH)CH2CH2OH (I) by organic acid anhydrides without the dehydration of the tertiary OH. I was also converted to the corresponding Me2C(OH)CH2CH2O2CR (II) and Me2C:CHCH2O2CR (III) and(or) CH2:CMeCH2CH2O2CR (IV). I (104 g.) and 102 g. Ac2O kept 1 hr. slightly below 70° and heated 1 hr. at 147° yielded 94% II (R = Me) (V), b20 105°, n20D 1.4300, d25 0.9993. I (38 g.) and 81 g. (C6H13CO)2O (VI) in 63 g. MePh refluxed 6 hrs. gave 87% II (R = C6H13) (VII), b0.15 87-93°, n20D 1.4412. I (114 g.), 150 cc. C6H6, and 110 g. Na2CO3 treated during 2 hrs. at 60° with 148 g. C6H13COCI (VIIa) and heated 2 hrs. at 60-70° yielded 137 g. VII, b0.60 105°, n20D 1.4411, d25 0.9336. I with BzCl gave similarly during 4 hrs. 68% II (R = Ph) (VIII), b0.9 127-8°, n2D0 1.5138, d25 1.0762. I (156 g.), 142 g. C17H35CO2H, 77 cc. xylene, and 3 g. Al2O3 refluxed 17 hrs. with the azeotropic removal of H2O yielded 116 g. II (R = C17H35), m. 40° (heptane). C8H17CH:CH(CH2)7CO2Me (169 g.) and 119 g. I distilled to remove 10 cc. I, treated with a piece of K, heated to 180° with the overhead removal of the MeOH, treated with 0.8 g. K in small pieces at intervals during 5 hrs., and distilled gave 70% II [R = C8H17CH:CH(CH2)7], b0.03 178-85°, n20D 1.4623, d25 0.9045. I (86 g.) added dropwise during 15 min. to 132.6 g. refluxing Ac2O yielded 115 g. IV (R = Me) (IX), b760 143-5°, n20D 1.4212, d25 0.9137. I (104 g.), 71 g. AcOH, 150 cc. C6H6, and 1 g. PhSO3H refluxed 5 hrs. with the azeotropic removal of H2O yielded 74 g. mixture, b40 63-72°, of 80% IX and 20% III (R = Me) (X). V (22.2 g.) in 50 cc. MePh refluxed with 1% iodine gave isoprene and only 30% mixture of IX and X; a similar run in C6H6 with C10H7SO3H yielded 50% mixture of 85% IX and 15% X. C6H13CO2H (65 g.), 57 g. I, 135 cc. C6H6, and 0.6 g. C10H7SO3H gave similarly 49 g. 80:20 mixture of IV (R = C6H13) (XI) and III (R = C6H13) (XII), b1.7 84-87°, n20D 1.4378, d25 0.879, and 18g. 65:35 mixture of XI and XII, b1.787-95°. BzOH (183 g.), 172 g. I, 300 cc. C6H6, and 1 g. PhSO3H refluxed 13 hrs. yielded after 11 g. forerun, b0.2 45-56°, n20D 1.4608, 34.5 g. mixture, b0.2 60-4°, n20D 1.5093, d25 1.0125, of IV (R = Ph) (XIII) and III (R = Ph) (XIV) containing mostly XIII, and 24 g. mixture, b0.2 64-5°, n20D 1.5118, of XIII and XIV containing mostly XIV. CH2: CMeCH2CH2OH (35 g.), 50 cc. CHCl3, and 29 g. C5H5N treated dropwise during 2 hrs. with 101 g. C17H35COCl in 100 cc. CHCl3 at 30-40° and refluxed 2 hrs. yielded 95 g. IV (R = C17H35), n20D 1.4518, d20 0.8670. Similarly was prepared from oleyl chloride 71% IV [R = C8H17CH:CH(CH2)7], b0.01 150-65°, n20D 1.4605, d20 0.8765. Ac2O (1326 g.) treated at reflux with 520 g. I yielded 797 g. Me2C (O2CR)CH2CH2O2CR’ (XV) (R = R’ = Me), b19 108-9°, n20D 1.4247, d25 1.0189, and a small amount of a mixture of 63% IX and 37% X. I (26 g.), 156 g. VI, and 80 g. MePh refluxed 13 hrs. yielded 61.5 g. XV (R = R’ = C6H13) (XVI), b0.1 128-34°, n20D 1.4418. I (36.4 g.) in 150 cc. CHCl3 and 100 cc. C5H5N treated dropwise with stirring during 3 hrs. with 119 g. VIIa at 30° and heated 5 hrs. at 60° yielded 100 g. XVI, b0.15 130-5°, n20D 1.4418, d25 0.9256. I (47 g.) with 135 g. BzCl gave similarly 31 g. distillate, b. 120-2°, containing mostly VIII and 82 g. XV (R = R’ = Ph), m. 34° (AmOH), d25 1.1212. VIII (104 g.) and 67 g. Ac2O heated 5 hrs. at 140° yielded 112 g. XV (R = Me, R’ = Ph), b0.85 131-2°, n20D 1.4974, d25 1.0820. Similarly were prepared the following XV (R = Me) (R’, % yield, b.p./mm. or m.p., n20D, and d20 given): C6H13, 94, 109-10°/0.6, 1.4360, 0.95874; C8H17CH:CH(CH2)7, 95, –, 1.4582, 0.92084; C17H35, 98, 24-5°, –, –.
Bulletin de la Societe Chimique de France published new progress about 5205-11-8. 5205-11-8 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Benzene,Ester, name is 3-Methylbut-2-en-1-yl benzoate, and the molecular formula is C12H14O2, Category: esters-buliding-blocks.
Referemce:
https://en.wikipedia.org/wiki/Ester,
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