1-haloalkadiene and a process for preparing the same and a process for preparing (9e, 11z)-9,11-hexadecadienyl acetate
AssigneeShin-Etsu Chemical Co., Ltd.
InventorsTomohiro Watanabe, Yuki Miyake, Takeshi Kinsho
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Abstract
A process to prepare (9E,11Z)-9,11-hexadecadienyl acetate with a good yield and high purity of the general formula (1): CH3—(CH2)3—CH═CH—CH═CH—(CH2)a—X.=The process includes a step of conducting a Wittig reaction between a haloalkenal of the general formula (2): OHC—CH═CH—(CH2)a—X, and a triarylphosphonium pentylide of the general formula (3): CH3—(CH2)3—CH−—P+Ar3, to obtain the 1-haloalkadiene, and the use of a (7E,9Z)-1-halo-7,9-tetradecadiene obtained by the process for a process of preparing (9E, 11Z)-9,11-hexadecadienyl acetate.
Claims4
A process for preparing (9E,11Z)-9,11-hexadecadienyl acetate of the following formula (7):
- said process comprising at least steps of:
- conducting a Wittig reaction between a (2E)-9-halo-2-nonenal of the following general formula (2-1):
- wherein X is a halogen atom, and a triarylphosphonium pentylide of the following general formula (3):
- CH3—(CH2)3—CH−—P+Ar3 (3),
- wherein Ar may be the same or different at each occurrence and is an aryl group having 6 or 7 carbon atoms, to obtain a (7E,9Z)-1-halo-7,9-tetradecadiene of the general formula (1-1):
- reacting the (7E,9Z)-1-halo-7,9-tetradecadiene (1-1) with magnesium to obtain a (7E,9Z)-7,9-tetradecadienyl magnesium halide;
- subjecting the (7E,9Z)-7,9-tetradecadienyl magnesium halide to an addition reaction with ethylene oxide to obtain (9E,11Z)-9,11-hexadecadienol of the following formula (6):
- conducting an acetylation reaction of (9E,11Z)-9,11-hexadecadienol (6) with an acylating agent to obtain (9E,11Z)-9,11-hexadecadienyl acetate.
A process for preparing a 1-haloalkadiene of the following general formula (1A):
- CH3—(CH2)3—CH═CH—CH═CH—(CH2)a′—X (1A),
- wherein X is a halogen atom, and a′ is an integer of from 6 to 15,
- said process comprising at least a step of:
- conducting a coupling reaction of an alkadienyl magnesium halide derived from a 1-haloalkadiene of the following general formula (4):
- CH3—(CH2)3—CH═CH—CH═CH—(CH2)c—X1 (4),
- wherein X1 is a halogen atom, and c is an integer of 3 or of from 5 to 12, with a dihaloalkane of the following general formula (5):
- X—(CH2)d—X (5),
- wherein X may be the same or different at each occurrence and is a halogen atom, and d is an integer of from 3 to 12, with a proviso that a sum of c and d is from 6 to 15, to obtain said 1-haloalkadiene.
Dependencies are inferred from the claim text.