Carbonic Acid → (2-Chloro-4,5-dihydroxyphenyl)phenylmethanone

HRID 462680

Reaction equation

HRID 462680 reaction equation
OC(O)=O.[Cl:5][C:6]1[CH:11]=[C:10]([O:12]C)[C:9]([O:14]C)=[CH:8][C:7]=1[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17].ClC1C=CC(OC)=C(OC)C=1.C(Cl)(=O)C1C=CC=CC=1.II.N1C=CC=CC=1OC(=O)C1C=CC=CC=1>FC(F)(F)C(O)=O>[OH:12][C:10]1[C:9]([OH:14])=[CH:8][C:7]([C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:17])=[C:6]([Cl:5])[CH:11]=1

Participants

8

Reactant 6

HCID 767Carbonic AcidHCID 807IodineHCID 7412Benzoyl chlorideHCID 280484-Chloro-1,2-dimethoxybenzene2×HCID 817610Pyridin-2-yl benzoateHCID 14118997(2-Chloro-4,5-dimethoxyphenyl)-phenylmethanone

Product 1

HCID 20396978(2-Chloro-4,5-dihydroxyphenyl)phenylmethanone

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The afore-mentioned dihydroxyketone can also be obtained in two stages analogously to Example 9a) and b). The (2-chloro-4,5-dimethoxyphenyl)-phenylmethanone required for this purpose can be obtained by acylating 4-chloro-1,2-dimethoxybenzene with benzoyl chloride in the presence of iodine. It is easier to obtain, however, if one equivalent of 4-chloro-1,2-dimethoxybenzene is heated in a bomb tube at 150° for 2 hours with 1.1 equivalents of (2-pyridinyl)-benzoate in trifluoroacetic acid. After working up and demethylation in a manner analogous to Example 9b), the desired (4,5-dihydroxy-2-chlorophenyl)-phenylmethanone is obtained.

Workup

  1. customcan be obtained
  2. customto obtain

Sources & evidence

ORD record
ord-bd89cd1a0bdb41ea97b474953466d323
Source dataset
uspto-grants-1985_05
Patent number
US04517184

Linked notes

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