Process for the preparation of 1-phenylindan photoinitiators
View Patent ↗The invention relates to a process for the preparation of a crystalline isomeric mixture of compounds of formulae (I) and (II) which process comprises the following steps: a) the slow addition of aluminium chloride, in portions, to a solution comprising 1,1,3-trimethyl-3-phenylindan and isobutyric acid halide in a suitable solvent at a reaction temperature of from −20° C. to 20° C., an isomeric mixture consisting of compounds of formulae (Ia) and (IIa) being obtained; b) enol chlorination of compounds (Ia) and (IIa), an isomeric mixture consisting of compounds of formulae (Ib) and (IIb) being obtained; c) hydrolysis of the chlorinated isomeric mixture from step b). The invention relates also to the preparation of the individual compounds (I) and (II).
1. A process for the preparation of a crystalline isomeric mixture of compounds of formulae I and II
which process comprises the following steps:
a) the slow addition of aluminium chloride, in portions in the course of from 2 to 3 hours, so that a local overdosing of aluminium chloride is avoided, to a solution comprising 1,1,3-trimethyl-3-phenylindan having a low oligomer content and isobutyric acid halide in 2-dichlorobenzene at a reaction temperature of from 0° C. to 5° C., an isomeric mixture consisting of compounds of formulae Ia and IIa being obtained
b) enol chlorination of compounds Ia and IIa, an isomeric mixture consisting of compounds of formulae Ib and IIb being obtained
c) hydrolysis of the chlorinated isomeric mixture from step b).
2. A process for the preparation of a crystalline compound of formula I
which process comprises
a) the slow addition of aluminium chloride, in portions in the course of from 2 to 3 hours, so that a local overdosing of aluminium chloride is avoided, to a solution comprising 1,1,3-trimethyl-3phenylindan having a low oligomer content and isobutyric acid halide in 12-dichlorobenzene at a reaction temperature of from 0° C. to 5° C., an isomeric mixture consisting of compounds of formulae Ia and IIa being obtained
b) enol chlorination of compounds Ia and IIa, an isomeric mixture consisting of compounds of formulae Ib and IIb being obtained
c) separation of the compound of formula Ib by recrystallisation and
d) hydrolysis of compound Ib.
3. A process for the preparation of a crystalline compound of formula II
which process comprises
a) the slow addition of aluminium chloride, in portions in the course of from 2 to 3 hours, so that a local overdosing of aluminium chloride is avoided, to a solution comprising 1,1,3-trimethyl-3-phenylindan having a low oligomer content and isobutyric acid halide in 12-dichlorobenzene at a reaction temperature of from 0° C. to 5° C., an isomeric mixture consisting of compounds of formulae Ia and IIa being obtained
b) enol chlorination of compounds Ia and IIa, an isomeric mixture consisting of compounds of formulae Ib and IIb being obtained
c) separation of the compound of formula Ib by recrystallisation and
d) hydrolysis of compound IIb.
4. A process according to claim 1 , wherein pure 1,1,3-trimethyl-3-phenylindan and isobutyric acid halide are first brought together and aluminium chloride is metered in slowly in the course of from 2 to 3 hours, so that a local overdosing of aluminium chloride is avoided.
5. A process according to claim 2 , wherein pure 1,1,3-trimethyl-3-phenylindan and isobutyric acid halide are first brought together and aluminium chloride is metered in slowly in the course of from 2 to 3 hours, so that a local overdosing of aluminium chloride is avoided.
6. A process according to claim 3 , wherein pure 1,1,3-trimethyl-3-phenylindan and isobutyric acid halide are first brought together and aluminium chloride is metered in slowly in the course of from 2 to 3 hours, so that a local overdosing of aluminium chloride is avoided.