Methyl cyclopentylphenylglycolate Chemical Properties

Boiling point:

120-127 °C(Press: 0.25 Torr)

Density 

1.160±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Oil

pka

12.28±0.29(Predicted)

color 

Clear Colorless to Pale Yellow

InChI

InChI=1S/C14H18O3/c1-17-13(15)14(16,12-9-5-6-10-12)11-7-3-2-4-8-11/h2-4,7-8,12,16H,5-6,9-10H2,1H3

InChIKey

FGMUSNHTKNGVQD-UHFFFAOYSA-N

SMILES

C(C1C=CC=CC=1)(C1CCCC1)(O)C(=O)OC

CAS DataBase Reference

19833-96-6(CAS DataBase Reference)

NIST Chemistry Reference

Alpha-cyclopentylmandelic acid, methyl ester(19833-96-6)

Safety Information

HS Code 

2932999000

Methyl cyclopentylphenylglycolate Usage And Synthesis

Chemical Properties

Pale Oil

Uses

Methyl α-Cyclopentylmandelate (cas# 19833-96-6) is a compound useful in organic synthesis.

Synthesis

2-Cyclopentyl-2-hydroxyphenylacetic acid (4.47 g, 20 mmol) and potassium carbonate (7.01 g, 50 mmol) were dissolved in N,N-dimethylformamide (50 mL). Iodomethane (8.64 g, 60 mmol) was slowly added to the mixture at room temperature. The reaction mixture was stirred continuously for 2 hours at room temperature. Upon completion of the reaction, the mixture was poured into water and extracted three times with hexane. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with the eluent being a 1.5:1 solvent mixture of hexane and dichloromethane, resulting in the pure product methyl 2-cyclopentyl-2-hydroxyphenylacetate (3.02 g, 64% yield). The structure of the product was confirmed by 1H NMR (CDCl3, 300 MHz): δ 1.32-1.37, 1.43-1.69 [8H, m, (CH2)4], 2.90 [1H, p, CHC(OH)], 3.74 (1H, s, OH), 3.77 (3H, s, CH3), 7.25-7.37, 7.63-7.65 (5H, m, Ph) ppm.

References

[1] Patent: US2007/123557, 2007, A1. Location in patent: Page/Page column 9

Methyl cyclopentylphenylglycolate(19833-96-6)Related Product Information

• Methyl glycolate
• Methyl bromoacetate
• Methyl acrylate
• Methyl methoxyacetate
• Methyl phenylacetate
• Methyl acetate
• METSULFURON METHYL
• Methyl cyanoacetate
• Methylparaben
• Bensulfuron methyl
• CYCLOPENTYLMAGNESIUM CHLORIDE
• Cyclopentanecarbaldehyde
• Methyl 3,5-dihydroxybenzoate
• Kresoxim-methyl
• alpha-Cyclopentylmandelic acid
• Benzoylformic acid
• Thiophanate-methyl
• LPHE-009