Nerol → (Z)-1,1-Diethoxy-6,10-dimethyl-5,9-undecadien-2-one

HRID 443372Notes

Reaction equation

[CH2:1](Br)/[CH:2]=[C:3](\[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])/[CH3:4].OC/C=C(/C)\CCC=C(C)C.[CH2:23]([O:25][CH:26]([O:35][CH2:36][CH3:37])[C:27](=[O:34])[CH2:28]C(OCC)=O)[CH3:24]>>[CH2:23]([O:25][CH:26]([O:35][CH2:36][CH3:37])[C:27](=[O:34])[CH2:28][CH2:1]/[CH:2]=[C:3](/[CH3:4])\[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])[CH3:24]

Participants

Reactant 3

HCID 643820Nerol

HCID 6087681Neryl bromide

HCID 11138577Ethyl 4,4-diethoxy-3-oxobutanoate

Product 1

HCID 13291922(Z)-1,1-Diethoxy-6,10-dimethyl-5,9-undecadien-2-one

Procedure

Reaction of neryl bromide which had been prepared from 31 g of nerol with 41.5 g of ethyl 4,4-diethoxyacetoacetate was carried out in the same manner as in Referential example 1 to yield 20 g of the desired product, b.p. 122° C./0.02 mmHg.

Sources & evidence

ORD record: ord-2668ea9f7d2b405c8e890d37d53122d1
Source dataset: uspto-grants-1981_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04260551

Reaction notes

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