Carbon Tetrachloride → 4-(3-Chloroprop-2-ynyl)phenylacetic acid methyl ester

HRID 484453Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]#[C:13]O)=[CH:7][CH:6]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:36]>O1CCCC1>[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]#[C:13][Cl:36])=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-(3-Hydroxyprop-2-ynyl)phenylacetic acid methyl ester (5.5 g, 0.027M) in tetrahydrofuran (110 ml) and carbon tetrachloride (110 ml) was added triphenylphosphine (7.81 g, 1.1 molar equivalents). The reaction mixture was heated at 60° C. for 3 h. After cooling, the solid obtained was removed by filtration and the mother liquors were concentrated under vacuum. The residue was purified by chromatography on silica gel using 50% diethyl ether in hexane as eluent to give the required product (5.35 g) as a colourless oil. δ (360 MHz, CDCl3) 3.62 (2H, s, CH2CO2CH3), 3.69 (3H, s, CH2CO2CH3), 4.36 (2H, s, CH2Cl), 7.23 (2H, d, J=8.2 Hz, ArH), 7.40 (2H, d, J=8.2 Hz, ArH).

Workup

temperatureAfter cooling
customthe solid obtained
customwas removed by filtration
concentrationthe mother liquors were concentrated under vacuum
customThe residue was purified by chromatography on silica gel using 50% diethyl ether in hexane as eluent

Sources & evidence

ORD record: ord-0a01fe2d75eb440d8740182fa2314539
Source dataset: uspto-grants-1993_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05231102

Reaction notes

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