Model Driven Engineering (MDE) is an important software development paradigm. Within this paradigm, models and constraints are essential components for expressing specifications of a software artefact. Object Constraint Language (OCL), a specification language that allows users to freely express constraints over different model features. However, one major issue is that the lack of OCL benchmarks makes difficult to evaluate existing and newly created OCL tools. In this paper, we present our initial idea about automatic OCL benchmark generation. The purpose of this paper is to show a developing idea rather than presenting a more formal and complete approach. Our idea is to use an OCL metamodel to sketch abstract syntax trees for OCL expressions, and solve generated typing constraints to produce the concrete OCL expressions. We illustrate this idea by using an example, discuss our work-in-progress and outline challenges to be tackled in the future.