received without purification, unless otherwise indicated. 1-Bromododecane,
pentaerythritol, and palladium on activated carbon (10% Pd, unreduced)
were purchased from Acros Organics. triethylene glycol monomethyl
ether, triethylene glycol, p-toluenesulfonyl chloride,
methyl 3,5-dihydroxybenzoate, benzaldehyde, 4-(dimethylamino)pyridine
(DMAP), p-toluenesulfonic acid monohydrate, N,N′-dicyclohexylcarbodiimide (DCC),
and benzyl bromide were products from Sigma-Aldrich. Dimethylformamide
(DMF), potassium carbonate (K2CO3), sodium hydroxide
(NaOH), sodium carbonate (Na2CO3), dichloromethane
(DCM), and methanol were purchased from Thermo Fisher Scientific.
Methyl 3,4-dihydroxybenzoate was bought from TCI Europe NV. Ethanol
(EtOH) and tetrahydrofuran (THF) were products from VWR International.
Potassium hydroxide (KOH) was bought from J.T.Baker, Avantor. Hydrochloric
acid (HCl, 37%) and potassium iodide (KI) were purchased from Merck.
Dry THF and dry DCM were obtained by passing solvents over activated
alumina columns in a MBraun MB SPS800 under nitrogen and stored under
argon. Ultrapure Milli-Q water (QPOD Milli-Q purification system,
18.2 MΩ) was used for the preparation of all nondeuterated aqueous
solutions.