1 to 2:
Always $A \subset \overline{A}$, so monotonicity of closure gives $\overline{A \cap U} \subset \overline{\overline{A} \cap U}$, without any assumptions.
So assume $x \in \overline{\overline{A} \cap U}$. We want to show that $x \in \overline{A \cap U}$. So let $O$ be an open neighbourhood of $x$. Then $O$ intersects $\overline{A} \cap U$. So for any $y$ in that intersection $O \cap \overline{A} \cap U$ we know that $O \cap U$ is a neighbourhood of $y$ (here we use $U$ is open), and so $y \in \overline{A}$ implies that $A \cap (O \cap U) \neq \emptyset$. So $O \cap (U \cap A) \neq \emptyset$, and as $O$ was an arbitrary neighbourhood of $x$, $x \in \overline{A \cap U}$. So we have the reverse inclusion as well.
2 to 1: suppose the equality holds for all $A$. We need to see that $U$ is open.
Idea: choose $A =X \setminus U$. Then the left hand side becomes $\overline{\emptyset} = \emptyset$, while the right hand side becomes $\overline{\overline{X \setminus U} \cap U}$. But this implies that no point can be in $\overline{X\setminus U} \cap U$. Or $\overline{X \setminus U} \subset X\setminus U$, which makes $X\setminus{U}$ closed and thus $U$ open.