Ammonium Chloride → HCID 10020919, compound

Participants

Reaction Conditions

Reaction Steps

2-Methoxyethoxy-methyl chloride (24.0 g, 192.7 mmol) is added dropwise to a 0° C. mixture of 25.0 g (94.6 mmol) of 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzoic acid, methyl ester and 27.5 g (212.4 mmol) of diisopropylethylamine in 50 ml of CH2Cl2 under a nitrogen atmosphere. The reaction is stirred at 25° C. for 24 hours and then poured onto saturated aqueous NH4Cl and the layers are separated. The aqueous layer is extracted with t-butylmethyl ether (2×150 ml). The combined organic extracts are washed with saturated aqueous NH4Cl, water and brine (2×), dried over Na2SO4, and concentrated in vacuo to give 33.2 g of the desired product as an orange oil. The product is pure enough to use in subsequent reactions. A sample can be purified by chromatography (flash, SiO2, 230-400 mesh, 29×6.5 cm, 15% t-butylmethylether-hexane) followed by Kugelrohr distillation.

Provenance & Evidence