(-)-Menthol → HCID 15346410, compound

HRID 975608Notes

Reaction equation

HRID 975608 reaction equation
[CH3:1][C@H:2]1[CH2:7][C@@H:6]([OH:8])[C@H:5]([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3]1.[CH2:12]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@@H:13]1[O:15][CH2:14]1>>[CH2:17]([O:16][CH2:12][C@H:13]([OH:15])[CH2:14][O:8][C@@H:6]1[CH2:7][C@H:2]([CH3:1])[CH2:3][CH2:4][C@H:5]1[CH:9]([CH3:11])[CH3:10])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 16666(-)-Menthol2×HCID 159746(-)-Benzyl (R)-glycidyl ether

Product 1

HCID 15346410HCID 15346410, compound

Procedure

That is, (2S)-3-l-menthoxypropane-1,2-diol can be obtained by adding (1R, 2S, 5R)-5-methyl-2-(1-methylethyl)cyclohexyl alcohol (hereinafter, is referred to as "l-menthol") to (R)-(-)-benzyl glycidyl ether [the compound of formula (II)]in the presence of a Lewis acid catalyst to provide (2S)-1-benzyloxy-2-hydroxy-3-{(1R, 2S, 5R)-[5-methyl-2-(1-methylethyl)cyclohexyl]oxy}propane [the compound of formula (III)], and hydrogenolyzing the compound in the presence of a palladium-carbon catalyst to eliminate the benzyl group.

Sources & evidence

ORD record
ord-c5c4440fc72d4398ab1358f43378b36b
Source dataset
uspto-grants-1997_03
Patent number
US05608119

Reaction notes

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