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filingDate 1959-02-27-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_d8a79052981dc24cf8c74fa36cf5240d
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publicationDate 1963-01-30-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-917006-A
titleOfInvention Reduction of organic compounds
abstract Organic compounds which contain an aldehyde, ketone or acid chloride group are reduced to alcohols by means of an adduct of an organic amine with borane BH3 or an alkyl or aryl borane BH2R or BHR2 which contains at least one hydrogen atom attached to the boron atom. In the case of certain compounds, which may be reduced without heating, the boranes of ammonia may also be employed as reducing-agents. The reduction may be carried out in a very wide variety of solvents including water and alcohols. In Example 1, acetone is reduced to isopropyl alcohol by means of dimethylamine-borane dissolved in diethyl ether. Acetone may also be reduced by means of piperidine-borane in aqueous solution. In Example 2, benzyl alcohol is obtained by reducing benzaldehyde with dimethylamineborane; and in Example 4, benzyl alcohol is obtained by reducing benzoyl chloride with trimethylamine-borane. Example 3 relates to the preparation of 2,2,2-trichloroethanol by reducing chloral hydrate with trimethylamineborane. In Example 5, cinnamyl alcohol is obtained by reduction of cinnamaldehyde, dissolved in glacial acetic acid, by means of dimethylamine borane. The method may also be used for the reduction of acetophenone, anisaldehyde, and 2,5-hexanedione. The adduct of ammonia and dimethyl-borane is mentioned as a useful reducing-agent.
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