Cyclohexanone → HCID 70608087, compound
Reaction equation
[C:1]1(=O)CCCCC1.[OH:8][C:9]1[C:14]([CH3:15])=[C:13]([OH:16])[C:12]([OH:17])=[C:11](C)[C:10]=1[OH:19]>>[OH:19][C:10]1[C:9]([OH:8])=[C:14]([CH3:15])[CH:13]([OH:16])[C:12]([OH:17])([CH3:1])[CH:11]=1Participants
Procedure
Attempts to form acetals from polyhydric phenols with two or more pairs of ortho-positioned hydroxy groups have been less successful. Soloway in U.S. Pat. No. 2,927,096 describes the preparation of resins from aldehydes and polyhydric phenols, such as 1,2,4,5-tetrahydroxybenzene and pentahydroxy benzene. Dallacker et al in Annalen, Band 719 (1968), pp. 112- 118 describe the preparation benzo[ 1.2-d: 4.5-d'] bis[ 1.3] dioxoles of the formula (III) wherein R is hydrogen, methoxy or allyl, by heating the corresponding mono-dioxole (IV) with chlorobromomethane in dimethyl formamide in the presence of potassium carbonate ##STR3## Kaye describes in the 13th Annual Report on Research, Petroleum Research Fund (1968) how reaction of catechol with cyclohexanone in the presence of toluene sulphonic acid in benzene gives only a 49% yield of the acetal, with some alkylation of the aromatic ring. Under the same conditions, no reaction took place between cyclohexanone and 1,2,4,5-tetrahydroxy- 3,6-dimethylbenzene. He showed, however, in Abstracts of Research Supported by the Petroleum Research Fund (196 ) p. 21 that 1,2,4,5-tetrahydroxy-3,5-dimethylbenzene formed an acetal (V) when heated with dichlorodiphenyl methane. ##STR4##
Sources & evidence
- ORD record
- ord-20b086c8dd6449b395765f90dfec0528
- Source dataset
- uspto-grants-1978_05
- Patent number
- US04092331
Reaction notes
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