Propionic Acid → 3-[2-Methyl-4-(2-methyl-benzyloxy)-phenyl]-hex-4-enoic acid ethyl ester

HRID 1993050Notes

Reaction equation

C(O)(=O)CC.[CH3:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[CH:10]=[CH:9][C:8]=1[CH:22]=[CH:23][CH:24](O)[CH3:25].[CH2:27]([O:29][C:30](OCC)([O:32]CC)[CH3:31])[CH3:28]>>[CH2:27]([O:29][C:30](=[O:32])[CH2:31][CH:22]([C:8]1[CH:9]=[CH:10][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:12][C:7]=1[CH3:6])[CH:23]=[CH:24][CH3:25])[CH3:28]

Participants

Reactant 3

HCID 1032Propionic Acid

HCID 66221Triethyl orthoacetate

HCID 686760914-[2-Methyl-4-(2-methyl-benzyloxy)-phenyl]-but-3-en-2-ol

Product 1

HCID 686755213-[2-Methyl-4-(2-methyl-benzyloxy)-phenyl]-hex-4-enoic acid ethyl esterYield 39%

Conditions

Temperature: 105 °C

Procedure

Propionic acid (cat.) was added to a solution of 31.5 (69 mg, 0.24 mmol) in 1,1,1-triethoxy-ethane (440 μL, 2.4 mmol). The reaction was stirred at 105° C. overnight. The solvent was removed under reduced pressure and the resulting residue was purified via radial chromatography (5% ethyl acetate in hexanes) to yield 33 mg (39%) of 3-[2-Methyl-4-(2-methyl-benzyloxy)-phenyl]-hex-4-enoic acid ethyl ester (31.6). LC/MSD m/e: 375.0 (M+Na).

Workup

customThe solvent was removed under reduced pressure
customthe resulting residue was purified via radial chromatography (5% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-ed10e0c8c4194af685487662f7c20384
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07649110B2

Reaction notes

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