Phenol → (1,1'-Biphenyl)-2,3'-diol

HRID 592124Notes

Reaction equation

HRID 592124 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=C(C)CCOC(C1C(=O)[O:17][C:18]2[C:23](C=1)=[CH:22][CH:21]=[CH:20][CH:19]=2)=O>>[CH:21]1[CH:22]=[C:23]([C:3]2[CH:4]=[CH:5][CH:6]=[C:1]([OH:7])[CH:2]=2)[C:18]([OH:17])=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 996PhenolHCID 867104572-oxo-2H-chromene-3-carboxylic acid 3-oxo-butyl ester

Product 1

HCID 33665(1,1'-Biphenyl)-2,3'-diol

Conditions

Temperature
80 °C

Procedure

The preparation of tagged diphenol 2.4 (3,3-bis(4-hydroxyphenyl)butyl 2-oxo-2H-chromene-3-carboxylate). Phenol (200 mmol) and a catalyst (e.g., Cs2.5H0.25DEAT0.25PW12O40, 0.5 g) can be combined under nitrogen in a 250 mL three necked flask equipped with a condenser and a magnetic stirrer and heated to 80° C. with stirring. A tagged ketone (20 mmol), such as 2-oxo-2H-chromene-3-carboxylic acid 3-oxo-butyl ester, can be added and diphenol 2.4 can be produced with high (e.g., approximately 96%) selectivity for the p,p-isomer.

Workup

  1. customequipped with a condenser and a magnetic stirrer

Sources & evidence

ORD record
ord-5b319cc0e4a94258a6a57db0ea703584
Source dataset
uspto-grants-2016_01
Patent number
US09238712B2

Reaction notes

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