Jacoby, who stands at 5 feet 11 inches and weighs 140 pounds, has gone missing in the midst of a record-breaking cold chill striking the US.
Ellen Pulda, a spokesman of the Maimonides School that Jacoby attends, reported that "the school is engaging all of its resources to aid Caleb's parents and the Brookline Police. Our entire school community is praying for Caleb's safe return."
On Tuesday, Jacoby's friends and Jewish community organizations were passing around fliers with the teenager's photograph, reports MassLive.
"He's a very quiet boy, he's also a very good one," said Efrat Lipschitz, Caleb's Hebrew teacher. "People really love him in school because he is a very good person."
On his Twitter account the columnist wrote, "we are so deeply, deeply grateful for everything being done to reunite us with our beloved son Caleb."
Those wishing to pray for the boy's safety are asked to pray for Calev Avraham ben Elisheva Rut.