Trimethyl orthoacetate → HCID 88219767, compound

HRID 1531598Notes

Reaction equation

[CH3:1]/[CH:2]=[CH:3]/[CH:4](O)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11](O)/[CH:12]=[CH:13]/[CH3:14].[C:17]([O:23]C)([O:21][CH3:22])(OC)[CH3:18]>C(CC(O)=O)(C)(C)C>[CH3:1][CH:2](/[CH:3]=[CH:4]/[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]/[CH:13]([CH3:14])[CH2:18][C:17]([O:21][CH3:22])=[O:23])[CH2:18][C:17]([O:21][CH3:22])=[O:23]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of tetradeca-2E,12E-diene-4,11-diol (5.0 g, 22.0 mmole), trimethyl orthoacetate (20 ml, 165 mmole), and t-butylacetic acid (0.1 g, 0.86 mmole) was heated to 120-140° C. for 3.0 hours with the slow distillation of the methanol formed during the reaction. The solution was cooled to 80° C. and the lower boiling materials were removed by vacuum distillation to afford dimethyl 3,14-dimethylhexadeca-4E,12E-diene-1,16-dioate (5.59 g, 75% yield) as an oil which was suitable for use in the subsequent reaction. C20H34O4 (338.49 g/mole). 1HNMR (500 MHz, CDCl3): 1.001 (d, 6H), 1.33-1.18 (m, 8H), 1.929 (dd, 4H), 2.257 (dt, 4H), 2.599 (dt, 2H), 3.634 (s, 6H), 5.32-5.27 (m, 2H), 5.43-5.36 (m, 2H) ppm. 13CNMR (125 MHz, CDCl3): 20.54, 28.99, 29.51, 32.52, 33.76, 41.89, 51.49, 129.74, 134.10, 173.22 ppm. IR (νmax(cm−1)): 2926(s), 2912(s), 2852(m), 1742(s), 1458(m), 1437(m), 1358(m), 1284(m), 1246(m), 1192(m), 1168(m), 1072(w), 1008(m), 970(m), 879(w), 839(w), 725(w). MS (m/z): 338(M+), 306, 275, 264, 257, 246, 233, 223, 215, 204, 191, 177, 163, 149, 135, 121, 108, 95, 81, 67, 55, 41.

Workup

customformed during the reaction
customthe lower boiling materials were removed by vacuum distillation

Sources & evidence

ORD record: ord-265e13fb7aa8481880d6c1aa161d545b
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06200254B1

Reaction notes

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