4'-Benzyloxybiphenyl-4-carboxylic acid 1-methylheptyl ester → 4'-Hydroxy-4-(1-methyl-heptyloxycarbonyl)biphenyl

HRID 1194644Notes

Reaction equation

HRID 1194644 reaction equation
[CH3:1][CH:2]([O:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24]CC3C=CC=CC=3)=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)=[O:11])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>C(O)C.[Pd]>[OH:24][C:21]1[CH:20]=[CH:19][C:18]([C:15]2[CH:16]=[CH:17][C:12]([C:10]([O:9][CH:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[O:11])=[CH:13][CH:14]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 1

HCID 543093414'-Benzyloxybiphenyl-4-carboxylic acid 1-methylheptyl ester

Product 1

HCID 147458464'-Hydroxy-4-(1-methyl-heptyloxycarbonyl)biphenylYield 80.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Next, S(+)-2-octanol (50 g, 0.38 mol) was dissolved in dry pyridine (150 ml), and to the solution was dropwise added under cooling, a solution of 4'-benzyloxybiphenyl-4-carboxylic chloride (112 g, 0.35 mol) dissolved in dry toluene (150 ml), followed by agitating the mixture at about 50°-60° C. for 2 hours, thereafter adding water (300 ml) and toluene (300 ml), agitating the mixture, washing the separated toluene layer with 6N-HCl, then with 2N-NaOH aqueous solution and further with water until the washing water became neutral, drying the toluene layer with anhydrous sodium sulfate and distilling off toluene to obtain 4'-benzyloxybiphenyl-4-carboxylic acid 1-methylheptyl ester (53 g), dissolving this ester (53 g, 0.13 mol) in ethanol (500 ml) and reducing it in the presence of palladium/carbon (Pd/C) 5 g) to obtain 4'-hydroxy-4-(1-methyl-heptyloxycarbonyl)biphenyl (34 g). (ii) Preparation of 4-octyloxycarbonyloxybenzoic chloride

Sources & evidence

ORD record
ord-856d65d3cfa845e988a3bcd4914e3093
Source dataset
uspto-grants-1989_03
Patent number
US04816181

Reaction notes

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