P-Cresol → HCID 89581301, compound

HRID 1501028Notes

Reaction equation

[OH:1][CH:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)[CH3:3].[CH:14]1[C:19](O)=[CH:18][CH:17]=[C:16]([CH3:21])[CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OC(C)C)=O)=O)(C)C>O1CCCC1>[C:16]1([CH3:21])[CH:17]=[CH:18][C:19]([O:1][CH:2]([C:4]2[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=2)[CH3:3])=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of methyl 4-(1-hydroxyethyl)benzoate (180 mg, 1.0 mmol), p-cresol (130 mg, 1.2 mmol), triphenylphosphine (393 mg, 1.5 mmol) and tetrahydrofuran (15 mL) were stirred at 20° C. for half an hour. Then azodicarboxylic acid diisopropyl ester (303 mg, 1.5 mmol) was added. The mixture was stirred at 20° C. for 12 hours. The resultant mixture was washed with water (20 mL×3). The organic phase was separated, dried over sodium sulfate, filtered, and concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1) to furnish methyl 4-(1-(p-tolyloxy)ethyl)benzoate as a colorless oil (100 mg, 37%).

Workup

stirringThe mixture was stirred at 20° C. for 12 hours
washThe resultant mixture was washed with water (20 mL×3)
customThe organic phase was separated
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customto give a residue
customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1)

Sources & evidence

ORD record: ord-8f7725e681994ce68d829ae39946dc05
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206128B2

Reaction notes

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