13-Methyl-10-oxa-15-pentadecanolide → 13,13-Dimethyl-10-oxa-15-pentadecanolide

HRID 617279Notes

Reaction equation

HRID 617279 reaction equation
[CH3:1][CH:2]1[CH2:18][CH2:17][O:16][C:14](=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[CH3:19]C1CCOC(=O)CCCCCCOCC1.CC1CCOC(=O)CCCCCCCOCC1>>[CH3:1][C:2]1([CH3:19])[CH2:18][CH2:17][O:16][C:14](=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 1056304713-Methyl-10-oxa-15-pentadecanolideHCID 1075270012-Methyl-9-oxa-14-tetradecanolideHCID 1079937511-Methyl-8-oxa-13-tridecanolide

Product 1

HCID 1082593413,13-Dimethyl-10-oxa-15-pentadecanolide

Procedure

Odorant: relatively weak, fruity-musk like, reminiscent of ambrettone.--IR (film): ν=1734 cm-1 (νC=O), 1118/1150 cm-1 (νasO--C--C), 1242 cm-1 (νasC--C(=O), 1365 cm-1 (d CH3), 1055 cm-1 (νC--O--C).--1H-NMR (CDCl3): δ=0.95 (s, 6H, 13-Me2), 1.33-1.40 (m, 8H, 4-H2 -7-H2), 1.49-1.55 (m, 4H, 8-,12-H2), 1.62 (mc, 2H, 3-H2), 1.76 (t, J=8.0 Hz, 2H, 14-H2), 2.32 (t, J=6.4 Hz, 2H, 2-H2), 3.38 (t, J=5.2 Hz, 2H, 11-H2), 3.47 (t, J=5.8 Hz, 2H, 9-H2), 4.16 (t, J=8.0 Hz, 2H, 15-H2). --13C-NMR (CDCl3): δ=23.94/24.56 (t, C-3,-7), 25.84/26.36/26.52 (t, C-4,-5,-6), 28.04 (2q, 13-Me2), 29.23 (t, C-8), 31.79 (s, C-13), 34.53 (t, C-2), 39.02 (t, C-14), 41.28 (t, C-12), 61.98 (t, C-15), 67.82/70.49 (t, C-9,-11), 173.83 (s, C-1). --MS (EI): m/z (%)=55 (100) [C4H7⊕ ]69 (92) [C5H9⊕ ], 113 (39) ]C8H17⊕ ], 139 (29) [M⊕ --C7H15O2 ], 155 (18) [M⊕ --C7H15O2 ], 197 (3) [M⊕ --CO--C2H4O], 241 (2) [M⊕ --CO], 270 (1) [M⊕].--C16H30O3 (270.41): calculated C 71.07, H 11.18; found C 70.89, H 11.11.

Sources & evidence

ORD record
ord-702e0ac71cf34f74acf618c0ffd64d21
Source dataset
uspto-grants-1999_09
Patent number
US05948812

Reaction notes

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