Hydrochloric Acid → (3-Chlorophenyl)(3-hydroxyphenyl)methanone

HRID 614701Notes

Reaction equation

HRID 614701 reaction equation
CCOCC.[Cl:6][C:7]1[CH:8]=[C:9]([C:13](=[O:22])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20]C)[CH:15]=2)[CH:10]=[CH:11][CH:12]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClC1C=CC=CC=1>[Cl:6][C:7]1[CH:8]=[C:9]([C:13](=[O:22])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 27576323-Chloro-3'-methoxybenzophenoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 20571875(3-Chlorophenyl)(3-hydroxyphenyl)methanone

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
60 °C

Procedure

26 of the ether obtained above in (1) and 60 cm3 of chlorobenzene are introduced into a 250 cm3 single-necked flask and 35 g of aluminium chloride are added a little at a time; the reaction mixture is then heated under reflux for 30 minutes, allowed to cool to about 60° C. and then poured onto a mixture of ice and concentrated hydrochloric acid (d = 1.18); this mixture is stirred for 1 hour and the solid is then filtered; the latter is washed with petroleum ether to free it from the last traces of chlorobenzene; the phenol thus obtained (20 g) melts at 104° C. and can be used without further purification.

Workup

  1. additionare introduced into a 250 cm3 single-necked flask
  2. temperaturethe reaction mixture is then heated
  3. temperatureunder reflux for 30 minutes
  4. filtrationthe solid is then filtered
  5. washthe latter is washed with petroleum ether

Sources & evidence

ORD record
ord-ddf85349cf16411ca56f3c6ec52b1637
Source dataset
uspto-grants-1979_03
Patent number
US04146385

Reaction notes

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