Methyl 3,5-bis(cyclohexylmethoxy)benzoate

Abstract

In the title compound, C22H32O4, the atoms of the methyl ester group and the alk­oxy O atoms are all coplanar with the central aromatic ring, with an r.m.s. deviation of 0.008 Å. Bonds to the methyl­ene and cyclo­hexyl groups are also very close to this plane, so that the mol­ecule is essentially flat, apart from the cyclo­hexyl groups. The mean planes through the cyclo­hexyl groups are tilted by 30.08 (9) and 36.14 (7)° with respect to the central aromatic ring. In the crystal, pairs of mol­ecules linked by C—H⋯O hydrogen bonds form planar units which are stacked along the a axis, with an average inter­planar distance of 3.549 (2) Å. Stacking appears to be stabilized by further weak C—H⋯O hydrogen bonds.

Synthesis of novel AB2 monomers for the construction of highly branched macromolecular architectures

“…In practice, it was more convenient to isolate the mono-alkylated product 12 by column chromatography (SiO 2 ) and then subject this intermediate to an alkylation with 11, giving the desired 13 as a crystalline solid upon trituration. 11 Hydrolysis of 13 to form 3 required higher temperatures compared with similar conditions used to prepare the standard benzyl ether monomer 1. 7 The difference in hydrolysis reactivity is proposed to be due to the hydrophobic cyclohexane rings reducing solubility of the parent methyl ester.…”

“…After the solvent was removed in vacuo, the resulting solid was purified by size exclusion chromatography in PhCH 3 to obtain 16 as a white foam (0.18 g, 63% Cyclohexane based monomer and corresponding branched material synthesis Methyl 3,5-bis(cyclohexylmethoxy)benzoate (13). 11 To methyl 3,5-dihydroxybenzoate (5.00 g, 29.7 mmol) in DMF (37.5 mL) was added K 2 CO 3 (8.50 g, 61.5 mmol) and the mixture was stirred at 25 ˚C for 2 h. Bromomethylcyclohexane (8.80 mL, 63.1 mmol) was added over 10 min, the reaction was heated at 80 ºC for 3 h. The reaction flask was cooled to 25 ˚C, EtOAc (100 mL) was added and the organic layer was washed with H 2 O (5 × 70 mL) and brine (70 mL). After drying over Na 2 SO 4 and removal of the solvent, the resulting product was purified by silica gel column chromatography (1:1 pet ether:Et 2 O) to separate the desired dialkylated product and the monoalkylated species.…”