Water → 4'-Benzyloxybiphenyl-4-carboxylic acid 1-methylheptyl ester

HRID 1194643Notes

Reaction equation

HRID 1194643 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21](Cl)=[O:22])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:24]>N1C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:13][CH:14]([O:24][C:21]([C:18]1[CH:19]=[CH:20][C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:10][CH:11]=2)=[CH:16][CH:17]=1)=[O:22])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:15][CH3:16]

Participants

5

Reactant 2

HCID 962WaterHCID 150849044'-(Phenylmethoxy)(1,1'-biphenyl)-4-carbonyl chloride

Product 1

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

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent2×

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

Workup

  1. additionto the solution was dropwise added
  2. temperatureunder cooling
  3. washwashing the separated toluene layer with 6N-HCl
  4. dry with materialdrying the toluene layer with anhydrous sodium sulfate
  5. distillationdistilling off toluene

Sources & evidence

ORD record
ord-b11f5d926bf44f5bba4ac2b24426d5d0
Source dataset
uspto-grants-1989_03
Patent number
US04816181

Reaction notes

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