Synthesis of 6-hydroxychroman-2-methanol derivatives

Details Synthesis of 6-hydroxychroman-2-methanol derivatives Synthesis of 6-hydroxychroman-2-methanol derivatives

1982-04-12

1984-01-03

Chan, Nicky

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549411, 549387, 548324, 568648, 568436, C07D31172, C07D31158

Patent

active

044243898

ABSTRACT:
A process for producing chroman, a compound of the formula, ##STR1## or an optically active compound thereof wherein R.sub.2, R.sub.3 and R.sub.4 are each a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group, which comprises reacting a compound of the formula, ##STR2## or an optically active compound thereof wherein A is an aryl group and R.sub.5 is a C.sub.1 -C.sub.4 alkyl group, with a compound of the formula, ##STR3## wherein R.sub.1 is a C.sub.1 -C.sub.3 alkyl group, X is a halogen atom and R.sub.2, R.sub.3 and R.sub.4 are as defined above, to obtain a compound of the formula, ##STR4## or an optically active compound thereof wherein A, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined above, reacting the resulting compound with methylmagnesium halide and then hydrolyzing to obtain the corresponding 4-aryl substituted 2-hydroxy-2-methylbutanal, or an optically active compound thereof, reducing the resulting compound to obtain a diol, or an optically active compound thereof, and then oxidizing the resulting compound to obtain a compound of the formula, ##STR5## or an optically active compound thereof wherein R.sub.2, R.sub.3 and R.sub.4 are as defined above, followed by reduction.
Chromans, the objective compounds of this invention, are an intermediate for the synthesis of tocopherols, particularly .alpha.-tocopherol.

REFERENCES:
patent: 4113740 (1978-09-01), Cohen et al.
patent: 4151177 (1979-04-01), Cohen et al.
patent: 4153614 (1979-05-01), Barner et al.
patent: 4234490 (1980-11-01), Barner et al.
patent: 4337346 (1982-06-01), Mukaiyama et al.
Mayer et al., Helvetica Chimica ACTA 46, 650, (1963).
Scott et al., Helvetica Chimica ACTA 59, 290, (1976).
Cohen et al., Helvetica Chimica ACTA 61, 837, (1978).
Barner et al., Helvetica Chimica ACTA 62, 2384, (1979).
Cohen et al., J. Am. Chem. Soc. 101, 6710, (1979).
Mukaiyama et al., Chemistry Letters 705, (1979).

Affiliated with

Also associated with

Rating

Synthesis of 6-hydroxychroman-2-methanol derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Synthesis of 6-hydroxychroman-2-methanol derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of 6-hydroxychroman-2-methanol derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1032802