Phenol → HCID 14570908, compound

HRID 1607291Notes

Reaction equation

HRID 1607291 reaction equation
C1([OH:7])C=CC=CC=1.[OH:8][C:9]1[C:14]2[C:15]([CH3:27])=[C:16]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[O:17][C:13]=2[C:12]([Cl:28])=[CH:11][C:10]=1[CH2:29][CH2:30][CH2:31][OH:32].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CC(C)=O>[OH:8][C:9]1[C:14]2[C:15]([CH3:27])=[C:16]([CH2:18][C:19]3[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)[O:17][C:13]=2[C:12]([Cl:28])=[CH:11][C:10]=1[CH2:29][CH2:30][C:31]([OH:7])=[O:32]

Participants

6

Reactant 4

HCID 996PhenolHCID 2724141Tetrabutylammonium FluorideHCID 14570907HCID 14570907, compoundHCID 131709961Jones' reagent

Product 1

HCID 14570908HCID 14570908, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of the silyated phenol derivative of (180) (Example 49) (400 mg, 0.84 mmol) in 10 mL acetone was added dropwise at 0° C. the Jones reagent. The reaction was monitored by tlc. The crude silylated acid after workup was treated with tetra-n-butyl ammonium fluoride as described before. The title compound was isolated by preparative tlc, mp 149°-151° C.

Sources & evidence

ORD record
ord-42438b614b1f4621a71c1d62e4b6f094
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

Loading…