참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Acetaldehyde | HCID 177 | — |
| 반응물 | Sodium ethoxide | HCID 2723922 | — |
| 반응물 | Phosphonium, [[3-(methoxycarbonyl)phenyl]methyl]triphenyl-, bromide | HCID 10051285 | — |
| 용매 | Ethanol | HCID 702 | — |
| 생성물 | Ethyl 3-(1-propenyl)benzoate | HCID 53648757 | — |
반응 단계
The preparation of XIII begins with the known methyl 3-(bromomethyl)benzoate. This halide is heated in xylene solution with triphenylphosphine to yield (3-methoxycarbonylbenzyl)triphenylphosphonium bromide. The phosphonium salt is converted to the ylide with sodium ethoxide in ethanol and the ylide caused to react with acetaldehyde to yield ethyl 3-(1-propenyl)benzoate. [Note that the ethyl ester has been obtained as a result of transesterification with solvent ethanol.] The ester is heated with N-bromosuccinimide in carbon tetrachloride for an extended period to yield ethyl 3-(3-bromo-1-propenyl)benzoate. This compound is treated with the anion derived from methyl methylthiomethyl sulfoxide as described in previous examples. The resulting dimethyl mercaptal S-oxide is hydrolyzed with acid catalysis to the aldehyde reagent XIII.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US04260771 |
|---|
| 출처 데이터셋 | uspto-grants-1981_04 |
|---|
| ORD ID | ord-63a6c990653c49fb9aac1405afe3b12d |
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| 출처 메모 | uspto-grants-1981_04 |
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