Benzophenone → 4,4'-(1,3-Dioxolane-2,2-diyl)diphenol

HRID 623255Notes

Reaction equation

HRID 623255 reaction equation
[C:1]1([C:7]2(C3C=CC=CC=3)OCC[O:8]2)C=CC=CC=1.[OH:18][C:19]1[CH:33]=[CH:32][C:22]([C:23]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[O:24])=[CH:21][CH:20]=1.C(C1C=CC=CC=1)(=O)C1C=CC=CC=1>>[OH:18][C:19]1[CH:33]=[CH:32][C:22]([C:23]2([C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=3)[O:8][CH2:7][CH2:1][O:24]2)=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 3102BenzophenoneHCID 691504,4'-DihydroxybenzophenoneHCID 2832302,2-Diphenyl-1,3-dioxolane

Product 1

HCID 147659554,4'-(1,3-Dioxolane-2,2-diyl)diphenol

Procedure

The preparation of 2,2-diphenyl-1,3-dioxolane from benzopheone under similar conditions is reported to give over 80% yield in only 5 hours reaction time, [M. Sulzbacher et al., J. Amer. Chem. Soc., 70, 2827 (1948)]. It is readily apparent that the synthesis of the ketal of 4,4'-dihydroxybenzophenone is accomplished less advantageously than the corresponding ketal of benzophenone.

Workup

  1. customto give over 80% yield in only 5 hours
  2. customreaction time, [M. Sulzbacher et al., J. Amer. Chem. Soc., 70, 2827 (1948)]

Sources & evidence

ORD record
ord-7ffac1569c974ecc9f5d1d93a94fc168
Source dataset
uspto-grants-1988_09
Patent number
US04774344

Reaction notes

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