Several series of chlorine-substituted rod-like liquid crystalline compounds have been synthesised containing a different number of lactate units in the chiral chain. Sequences of phases and phase transition temperatures were determined by differential scanning calorimetry, polarising optical microscopy and X-ray diffraction studies. Depending on the molecule structure, the materials possess a rich variety of mesophases, i.e. the paraelectric chiral smectic A (SmA*), ferroelectric chiral smectic C (SmC*) and antiferroelectric smectic C (SmC A *) phases. Additionally, some compounds with one and two lactate groups exhibit the frustrated antiferroelectric twist grain boundary (TGB A ) and smectic Q (SmQ) phases, respectively. The existence of the SmQ phase ordered in two directions was confirmed by X-ray diffraction on a non-oriented sample. The effects of the non-chiral chain length and number of the chiral lactate groups on the mesomorphic properties, spontaneous polarisation, spontaneous tilt angle and complex permittivity have been studied and discussed.