Cetalox → Sclareol

HRID 659928Notes

Reaction equation

[CH3:1][C:2]12[CH2:14][CH2:13][CH:12]3[C:7]([CH3:17])([CH2:8][CH2:9][CH2:10][C:11]3([CH3:16])[CH3:15])[CH:6]1[CH2:5][CH2:4][O:3]2.C[C@@]12[C@H:28]3CC[O:31][C@:27]3(C)[CH2:26][CH2:25][C@H]1C(C)(C)CCC2>>[CH3:17][C@@:7]12[C@@H:6]([CH2:5][CH2:4][C@@:27]([OH:31])([CH:26]=[CH2:25])[CH3:28])[C@@:2]([OH:3])([CH3:1])[CH2:14][CH2:13][C@H:12]1[C:11]([CH3:15])([CH3:16])[CH2:10][CH2:9][CH2:8]2

Participants

Reactant 2

HCID 107166Cetalox

HCID 10857465(-)-Ambroxide

Product 1

HCID 163263Sclareol

Procedure

Dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan (occasionally referred to as “Ambroxan (trademark)”) is an aroma chemical with satisfactorily long-lasting properties that is produced via chemical conversion mainly from sclareol extracted from Salvia sclarea. FIG. 1 shows a process for producing dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan from sclareol. As shown in FIG. 1, decahydro-2-hydroxy-2,5,5,8a-tetramethylnaphthaleneethanol and sclareolide (decahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan-2(1H)-one) are known as dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan intermediates. Also, a cyclic ether compound (8α,13-oxido-12,13-dehydro-15,16-dinorlabdane) is known as a dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan intermediate, although it is not shown in FIG. 1.

Sources & evidence

ORD record: ord-49cc65102bf44704aeb8d496d0eab406
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084237B2

Reaction notes

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