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XU ET AL.
C20H10D4O4 (M + H) 323.12159, found 323.12177.
Elemental analysis calculated for C20H10D4O4:
C: 74.34%, H: 3.12%, D: 2.49%, Found C: 74.23%,
H: 3.16%, D: 2.50%.
3.38 (s, 6H). 13C NMR (120 MHz, CDCl3), δ ppm:
167.6, 131.9, 130.7 (t, J = 24.0 Hz), 128.7 (t, J =
24.0 Hz), 70.3, 64.8, 59.1. HRMS (ESI) calculated for
C14H14D4O6 (M + H) 287.14272, found 287.14328.
Elemental analysis calculated for C14H14D4O6: C:
58.56%, H: 4.91%, D: 2.81%, Found C: 58.40%, H:
4.95%, D: 2.82%.
4.3.9 | Dioctyl phthalate-3,4,5,6-D4
98.1% yield, 99.5 atom% D.1H NMR (500 MHz, CDCl3)
δ ppm 4.26 to 4.29 (m, 4H), 1.69 to 1.74 (m, 4H), 1.36
to 1.41 (m, 4H), 1.26 to 1.30 (m, 16H), 0.85 to 0.88
(m, 6H). 13C NMR (120 MHz, CDCl3), δ ppm: 167.8,
132.3, 130.5 (t, J = 22.8 Hz), 128.5 (t, J = 22.8 Hz), 66.0,
31.9, 29.4, 29.2, 28.6, 26.1, 22.7, 14.2. HRMS (ESI)
calculated for C24H34D4O4 (M + H) 395.30939,
found 395.31039. Elemental analysis calculated for
C24H34D4O4: C: 72.92%, H: 8.67%, D: 2.04%, Found
C: 72.78%, H: 8.71%, D: 2.05%.
4.3.13 | Di(2-ethoxyethyl) phthalate-
3,4,5,6-D4
98.1% yield, 99.5 atom% D.1H NMR (500 MHz, CDCl3)
δ ppm 4.39 to 4.47 (m, 4H), 3.69 to 3.74 (m, 4H), 3.47 to
3.67 (m, 4H), 1.13 to 1.21 (m, 6H). 13C NMR (120 MHz,
CDCl3), δ ppm: 167.7, 132.0, 130.7 (t, J = 24.0 Hz), 128.7
(t, J = 24.0 Hz), 68.2, 68.1, 66.7, 66.6, 65.0, 64.9, 15.2.
HRMS (ESI) calculated for C16H18D4O6 (M + H)
315.17402, found 315.17484. Elemental analysis
calculated for C16H18D4O6: C: 60.97%, H: 5.75%,
D: 2.56%, Found C: 60.93%, H: 5.76%, D: 2.56%.
4.3.10 | Di(2-ethylhexyl) phthalate-3,4,5,6-D4
99.1% yield, 99.5 atom% D.1H NMR (500 MHz, CDCl3)
δ ppm 4.17 to 4.24 (m, 4H), 1.62 to 1.69 (m, 2H), 1.36
to 1.44 (m, 4H), 1.28 to 1.35 (m, 12H), 0.87 to 0.92
(m, 12H). 13C NMR (120 MHz, CDCl3), δ ppm: 167.9,
132.4, 130.5 (t, J = 25.2 Hz), 128.5 (t, J = 24.0 Hz), 68.2,
38.8, 30.4, 29.0, 23.8, 23.1, 14.2, 11.1. HRMS (ESI)
calculated for C24H34D4O4 (M + H) 395.30939,
found 395.30969. Elemental analysis calculated for
C24H34D4O4: C: 72.92%, H: 8.67%, D: 2.04%, Found
C: 72.79%, H: 8.70%, D: 2.05%.
4.3.14 | Di(2-butoxyethyl) phthalate-
3,4,5,6-D4
1
97.9% yield, 99.5 atom% D. H NMR (500 MHz, CDCl3)
δ ppm 4.44 (t, J = 5.0 Hz, 4H), 3.70 (t, J = 5.0 Hz,
4H), 3.47 (t, J = 7.0 Hz, 4H), 1.52 to 1.58 (m, 4H),
1.31 to 1.39 (m, 4H), 0.89 (t, J = 7.5 Hz, 6H). 13C
NMR (120 MHz, CDCl3), δ ppm: 167.6, 132.0, 130.7
(t, J = 24.0 Hz), 128.7 (t, J = 24.0 Hz), 71.3, 68.4,
64.9, 31.8, 19.3, 14.0. HRMS (ESI) calculated for
C20H26D4O6 (M + H) 371.23662, found 371.23691. Ele-
mental analysis calculated for C20H26D4O6: C: 64.71%,
H: 7.06%, D: 2.17%, Found C: 64.58%, H: 7.10%, D:
2.18%.
4.3.11 | Di-n-nonyl phthalate-3,4,5,6-D4
1
98.3% yield, 99.5 atom% D. H NMR (500 MHz, CDCl3)
δ ppm 4.28 (t, J = 7.0 Hz, 4H), 1.68 to 1.74 (m, 4H), 1.37
to 1.39 (m, 4H), 1.25 to 1.33 (m, 20H), 0.86 (t, J = 7.0 Hz,
6H). 13C NMR (120 MHz, CDCl3), δ ppm: 167.8, 132.3,
130.5 (t, J = 24.0 Hz), 128.5 (t, J = 24.0 Hz),65.9, 31.9,
29.6, 29.4, 29.3, 28.6, 26.1, 22.8, 14.2. HRMS (ESI)
calculated for C26H38D4O4 (M + H) 423.34069, found
423.34177. Elemental analysis calculated for C26H38D4O4:
C: 73.77%, H: 9.04%, D: 1.90%, Found C: 73.70%,
H: 9.09%, D: 1.91%.
4.3.15 | Di(4-methyl-2-pentyl) phthalate-
3,4,5,6-D4
1
98.6% yield, 99.5 atom% D. H NMR (500 MHz, CDCl3)
δ ppm 5.21 to 5.24 (m, 2H), 1.65 to 1.74 (m, 4H),
1.36 to 1.38 (m, 2H), 1.33 (d, J = 6.0 Hz, 6H), 0.93
(t, J = 7.0 Hz, 12H). 13C NMR (120 MHz, CDCl3),
δ ppm: 167.2, 167.1, 132.8, 130.3 (t, J = 22.8 Hz), 128.4
(t, J = 22.8 Hz), 71.1, 71.0, 45.2, 45.1, 24.8, 24.7, 23.0,
22.9, 22.6, 22.5, 20.3. HRMS (ESI) calculated for
C20H26D4O4 (M + H) 339.24679, found 339.24765. Ele-
mental analysis calculated for C20H26D4O4: C: 70.81%,
H: 7.72%, D: 2.37%, Found C: 70.74%, H: 7.75%, D:
2.38%.
4.3.12 | Di(2-methoxyethyl) phthalate-
3,4,5,6-D4
1
98.5% yield, 99.5 atom% D. H NMR (500 MHz, CDCl3)
δ ppm 4.43 to 4.45 (m, 4H), 3.66 to 3.68 (m, 4H),