Ethanol → Ethyl 3,3-dimethylpent-4-enoate

HRID 359170

Reaction equation

C(OC(OCC)(O[CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])C)C.[C:15]1([OH:21])C=CC=C[CH:16]=1.[CH2:22]([OH:24])[CH3:23]>>[CH3:10][C:9]([CH3:11])([CH:8]=[CH2:7])[CH2:23][C:22]([O:21][CH2:15][CH3:16])=[O:24]

Participants

Reactant 3

HCID 702Ethanol

HCID 996Phenol

HCID 133214151-(1,1-Diethoxyethoxy)-3-methylbut-2-ene

Product 1

HCID 82262Ethyl 3,3-dimethylpent-4-enoateYield 72%

Procedure

A mixture of 2.02 g of 1,1-diethoxy-1-(3-methyl-2-buten-1-yloxy)ethane and 20 mg of phenol was heated for 12 hours at 150°-160°, during which time ethanol was evolved. Distillation of the residue gave 1.12 g (72% yield) of ethyl 3,3-dimethyl-4-pentenoate, b.p. 80°-83°/57 mm.

Workup

distillationDistillation of the residue

Sources & evidence

ORD record: ord-6660faa2fb4841c8a261dc641d29db7d
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04999451

Linked notes

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