Isoprene → (1-Hydroxycyclohex-3-en-1-yl)(phenyl)methanone

Reaction equation

[C:1]1([C:7](=[O:15])[C:8]([O:10][Si](C)(C)C)=[CH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16]=[CH:17][C:18](=C)[CH3:19]>>[C:7]([C:8]1([OH:10])[CH2:19][CH2:18][CH:17]=[CH:16][CH2:9]1)(=[O:15])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 6557Isoprene

HCID 129213841-Phenyl-2-[(trimethylsilyl)oxy]prop-2-en-1-one

Product 1

HCID 19935299(1-Hydroxycyclohex-3-en-1-yl)(phenyl)methanone

Procedure

If the 1-phenyl-2-trimethylsiloxyprop-2-en-1-one is reacted with isoprene instead of butadiene, an analogous procedure gives an oily product which, after bulb tube distillation (150°/0.06 mm Hg), gave the following analysis:

Workup

customan analogous procedure gives an oily product which
distillationafter bulb tube distillation (150°/0.06 mm Hg)
customgave the following analysis

Sources & evidence

ORD record: ord-cc4c55965a31479580c8747e6ea327e0
Source dataset: uspto-grants-1985_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04498964

Reaction notes

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