[(3,7-Dimethyl-6-octenyl)oxy]acetaldehyde → HCID 11107697, compound

HRID 1767445Notes

Reaction equation

HRID 1767445 reaction equation
[CH2:1](OCC=O)CC(CCC=C(C)C)C.[CH3:15][C:16]1([CH3:31])[C:24]2[CH:23]=[C:22]3[O:25][CH2:26][C:27](=[O:30])[CH2:28][O:29][C:21]3=[CH:20][C:19]=2[CH2:18][CH2:17]1>>[CH3:31][CH:16]([CH2:15][CH3:1])[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]2[O:25][CH2:26][C:27](=[O:30])[CH2:28][O:29][C:21]=2[CH:20]=1

Participants

3

Reactant 2

HCID 61401[(3,7-Dimethyl-6-octenyl)oxy]acetaldehydeHCID 10988125HCID 10988125, compound

Product 1

HCID 11107697HCID 11107697, compound

Procedure

Odor: Marine, animalic, civet-like, floral-aldehyde odor, also somewhat reminiscent of citronelloxyacetaldehyde ([3,7-dimethyl-6-octenyl]oxy-acetaldehyde). -IR (film): ν=1502/1435/1460/1580 cm−1 (ν C═C, Ar), 1265/1304/1202 cm−1 (ν ring), 1051 cm−(ν C—O—C), 1741 cm−1 (ν C═O). -1H-NMR (CDCl3): δ=0.87 (t, J=7.2 Hz, 3H, 5′-H3), 0.91 (d, J=6.4 Hz, 3H, 3′-Me), 1.18 (mc1 1H, 2′-Hb), 1.34-1.43 (m, 3H, 2′-Ha, 4′-H2), 1.56-1.62 (m, 1H, 3′-H), 2.48 (ddd, J=14.0, 10.0, 6.4 Hz, 1H, 1′-Ha), 2.56 (ddd, J=14.0, 10.4, 5.2 Hz, 1H, 1′-Hb), 4.67 (d, J=2.4 Hz, 4H, 2-,4-H2), 6.78 (dd, J=8.2, 2.4 Hz, 1H, 8-H), 6.82 (d, J=2.0 Hz, 1H, 6-H), 6.90 (d, J=8.4 Hz, 1H, 9-H). -13C-NMR (CDCl3): δ=11.14 (q, C-5′), 18.93 (q, 3′-Me), 29.18 (t, C-4′), 32.42 (t, C-1′), 33.84 (d, C-3′), 38.23 (t, C-2′), 22.38 (t, C-4′), 30.90/31.26 (2t, C-2′,-3′), 75.35/75.64 (2t, C-2,-4), 120.27/120.51 (2d, C-6,-9), 123.45 (d, C-8), 139.11 (s, C-7), 146.00/147.86 (2s, C-5a,-9a), 204.72 (s, C-3). -MS (EI): m/z (%)=77 (21) [C8H5+], 92 (14) [C7H8+], 135 (11) [M+-C5H11—C2H2O], 149 (16) [M+-C5H11—CO], 177 (100) [M+-C5H11], 191 (4) [M+-C4H9], 205 (7) [M+-C3H7], 248 (45) [M+].

Sources & evidence

ORD record
ord-011c990a5eaa43898fcb4bc95c078fad
Source dataset
uspto-grants-2007_06
Patent number
US07235519B2

Reaction notes

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