METHYL 2-(3-HYDROXYPROP-1-YNYL)BENZOATE

METHYL 2-(3-HYDROXYPROP-1-YNYL)BENZOATE Property

storage temp. 

2-8°C

Safety

Hazard Codes 

Xi

Hazard Note 

Irritant

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

METHYL 2-(3-HYDROXYPROP-1-YNYL)BENZOATE Chemical Properties,Usage,Production

Synthesis

Example 1: Preparation of tert-butoxy-[4-(4-methoxy-3,5-dimethylphenyl)-2-methyl-1-oxo-1,2-dihydroisoquinolin-3-yl]-acetic acid Step A: Synthesis of methyl 2-(3-hydroxyprop-1-ynyl)-benzoate Methyl 2-iodobenzoate (88.0 g, 335.9 mmol), 2-propyn-1-ol (28.3 g, 503.8 mmol), copper iodide (1.2 g, 6.7 mmol), Pd(PPh3)2Cl2 (7.0 g, 10.0 mmol), and triethylamine (68.0 g, 671.8 mmol) were suspended in acetonitrile (1 L). The solution was bubbled with N2 for 20 min to deoxidize. Subsequently, the reaction mixture was stirred at reflux for 3 h under N2 protection. After completion of the reaction, the mixture was filtered and the filtrate was concentrated to dryness. The residue was purified by column chromatography to afford the target product methyl 2-(3-hydroxyprop-1-ynyl)-benzoate (58.8 g, 92.0% yield). 1H NMR (400 MHz, d6-DMSO): δ 2.48 (t, J = 6.2 Hz, 1H), 3.88 (s, 3H), 4.52 (d, J = 5.6 Hz, 2H), 7.32 (t, J = 7.6 Hz, 1H), 7.41 (t, J = 7.6 Hz, 1H), 7.51 (d, J = 7.6 Hz, 1H), 7.90 (d, J = 7.6 Hz, 1H), 7.90 (d, J = 7.6 Hz, 1H). 7.90 (d, J = 7.2 Hz, 1H).

References

[1] Patent: WO2012/102985, 2012, A1. Location in patent: Page/Page column 94
[2] Doklady Chemistry, 1985, vol. 283, p. 212 - 214
[3] Dokl. Akad. Nauk SSSR Ser. Khim., 1985, vol. 283, # 3, p. 630 - 633
[4] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 996 - 1005
[5] Organic Letters, 2018, vol. 20, # 10, p. 3034 - 3038