Lithium hydroxide, monohydrate → 2-Isobutyl-succinic acid-4-t-butyl ester

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Reaction Steps

2-Isobutylsuccinic acid-4-t-butyl ester-1-methyl ester (11.1 g, 45.4 mmol) and LiOH.H2O (2.0 g, 47.7 mmol) are stirred in 180 mL of 3:1 IPA/H2O at room temperature overnight. The reaction mixture is extracted with Et2O (3×25 mL). The aqueous phase is acidified to pH=4, with saturated KH2PO4 and extracted with Et2O (3×50 mL). The Et2O is dried over MgSO4, and evaporated to give 8.0 g (77% yield) of 2-isobutyl-succinic acid-4-t-butyl ester as an oil. NMR (H1, 400 MHz, CDCl3) δ 0.9 (6H, m); δ 1.3 (1H, m); δ 1.4 (9H, s); δ 1.6 (2H, m); δ 2.3 (1H, dd); δ 2.6 (1H, dd); δ 2.8 (1H, m).

Provenance & Evidence