Methanol → 4-(4'-Hydroxyphenyl)-2-butanone

HRID 634888

Reaction equation

C[C:2]1[C@@H:19](OC([C@H](O)[C@@H](NC(C2C=CC=CC=2)=O)C2C=CC=CC=2)=O)[CH2:18][C@:14]2(O)[C:15](C)(C)[C:3]=1[C@@H](OC(C)=O)C([C@@]1(C)[C@H:12]([C@@H:13]2OC(C2C=CC=CC=2)=O)[C@:11]2([O:53]C(C)=O)CO[C@@H:10]2C[C@@H]1O)=O.C[OH:64]>>[CH3:10][C:11]([CH2:12][CH2:13][C:14]1[CH:18]=[CH:19][C:2]([OH:64])=[CH:3][CH:15]=1)=[O:53]

Participants

Reactant 2

HCID 887Methanol

HCID 36314Paclitaxel

Product 1

HCID 216484-(4'-Hydroxyphenyl)-2-butanone

Procedure

Taxus wallichiana known as the Himalayan yew is available in India. The applicants have investigating the different parts of this plant from different Himalayan regions of India for isolation of naturally occurring analogues of taxol, its important precursors and other biologically active compounds. During the course of investigation the applicants have isolated 2 compounds of 4-aryl-2-butanol namely betuligenol having formula C10H14O2, mp 69-70° C., [α]n+20 (C1, MeOH) and betuliloside having formula C16H24O7 mp 187-188°, [α]n+22° (C1, MeOH) from the leaves of T. wallichiana.

Sources & evidence

ORD record: ord-155f7e0dea044e9eaeba54feb561dae2
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06184367B2

Linked notes

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