JPS62145036A - Optically active phenyl ehter - Google Patents

Abstract

NEW MATERIAL:An optically active phenyl ether compound of formula I (X is halogen; n is 3-12; * remarks asymmetric carbon). EXAMPLE:4-Methyldecyl-4'-bromophenyl ether. USE:Intermediate of ferroelectric liquid crystal. PREPARATION:For example, 4-methylalkanol is sulfonated and allowed to react with 4-halogenophenol to give the compound of the formula.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a specific optically active phenyl ether compound, and more particularly to a halogenated phenyl ether compound having an alkyl group having an asymmetric carbon.

Alkoxybenzene derivatives with asymmetric carbon atoms have attracted particular attention in recent years as intermediates for liquid crystal chemicals.
Alkoxybiphenyl compounds, alkoxyphenylpyrimidine compounds, alkoxybenzoic acid derivatives, and the like are known as ferroelectric smectic liquid crystal chemicals.

The alkoxy group in these liquid crystal compounds is 6
-Methyloctoxy group, 2-methylbutoxy group, etc. are known, but these compounds have problems such as an inappropriate usable temperature range or poor stability, making them difficult to use for practical purposes. It wasn't something.

For this reason, ferroelectric liquid crystal compounds, including the basic skeleton of the compound, are currently being studied.

As a result of extensive studies on alkoxybenzene compounds having asymmetric carbon atoms, the present inventors have found the following general formula (
It has been found that the compound represented by I) has excellent optical activity.

Furthermore, since the compound represented by the general formula CI) has a highly reactive halogen atom as a nuclear substituent, it is expected to be an intermediate for ferroelectric liquid crystal compounds.

H3 (In the formula, X represents a halogen atom, n represents 3 to 12, and * represents an asymmetric carbon.) Hereinafter, the present invention will be explained in more detail.

Examples of the halogen atom represented by X include chlorine, bromine, iodine and fluorine, and compounds in which X is bromine are particularly preferred. Further, n represents 3 to 12, but compounds of 4 to 10 are particularly preferred.

The compound represented by the above general formula (I) can be prepared, for example, by converting 4-methylalkanol into a sulfonic acid ester, and then producing 4-
It can be easily produced by a well-known etherification reaction such as reaction with a halogenated phenol.

Next, the present invention will be explained by examples.

Example 1 172 g (I, 0 mol) of 4-methyldecanol and 151.5 g (I, 5 mol) of triethylamine were dissolved in 1300 ml of dichloromethane and cooled to 0 to -10°C.

Methanesulfonyl chloride 149g (I, 3 mol)
was added dropwise, and after the addition, the mixture was stirred at the same temperature for 2 hours.

10,100 O of dichloromethane was added, and the mixture was washed successively with ice water, 10% hydrochloric acid, saturated aqueous sodium carbonate, and saturated brine, dried over magnesium sulfate, and the solvent was removed to produce 4-methyldecyl methanesulfonate.

125 g of the above 4-methyldecyl methanesulfonate (0
, 5 mol), 4-bromophenol 95.1 g (0
, 55 mol), powdered sodium hydroxide 30 g (0
, 75 mol) and dioxane were taken and stirred for 8 hours under reflux. After confirming the disappearance of the sulfonic acid ester by chromatography, the produced sodium chloride was filtered off. The filtrate was desolvented, and the resulting residue was extracted with 10,100 O of toluene, and the toluene solution was washed with 5% hydrochloric acid and then with saturated brine, and the solvent was removed.

Distillation was carried out under reduced pressure to obtain 4-methyldecyl-4'-bromophenyl ether as a distillate with a boiling point of 16 s°C/1 mmHg.

As a result of infrared spectroscopy, the obtained product had the following characteristic absorption, confirming that it was the desired product.

1590cm-'S1590cm-' and 820cm-
' (benzene ring), 1380c11-' (methyl group), 1250cm-' (ether) Further, the optical rotation of the obtained product is shown below.

[α) O-+2.84' (Chloroform) Example 2 The boiling point was The desired product, 4-methyldodecyl-4'-bromophenyl ether, was obtained as a distillate at 175°C/1 auwHg.

As a result of infrared spectroscopic analysis, the obtained product had the following characteristic absorption, and was confirmed to be the desired product.

1590cm-1,1590cm-' and 820cm-
' (benzene ring), 1380cm-' (methyl group)
, 1250 cm-' (ether) Also, the optical rotation of the obtained product is shown below.

[α) D = +1.99' (Chloroform) Procedural amendment dated October 3, 1985 1. Indication of the case Patent application No. 1986-286322 3. Person making the amendment Relationship to the case Patent applicant Seiko Epson shares Company Adeca Argus Chemical Co., Ltd. 4, Agent 5-2-13 Shirahata, Urawa City, Saitama Prefecture Adeca Argus Chemical Co., Ltd. 5, Date of amendment order Voluntary amendment 6, Detailed explanation of the invention in the specification subject to amendment column.

7. Contents of amendment (I) “4-methyldesyloxy-” on page 3, line 14 of the specification
4-bromo” to “4-methyldecyl-4°-bromo”
and correction.

(3) 11590cm-', 1590, page 4, line 20
Correct cm-' J to r 1590 cm-' J.

(4) r 1590cm-', 159 on page 5, line 15
Correct 0cm-' J to 11590cm-' J.

that's all

Claims (1)

[Claims] An optically active phenyl ether compound represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, X represents a halogen atom, n represents 3 to 12, and * represents an asymmetric carbon.)