HCID 178439125, compound → HCID 178444280, compound

HRID 370367Notes

Reaction equation

HRID 370367 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24](Cl)=[O:25])=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:27]([C:30]1[CH:35]=[CH:34][C:33]([C@H:36]2[CH2:41][CH2:40][C@H:39]([OH:42])[CH2:38][CH2:37]2)=[CH:32][CH:31]=1)[CH2:28][CH3:29]>C1C=CC=CC=1.N1C=CC=CC=1>[CH2:27]([C:30]1[CH:35]=[CH:34][C:33]([C@H:36]2[CH2:37][CH2:38][C@H:39]([O:42][C:24]([C:21]3[CH:20]=[CH:19][C:18]([C:15]4[CH:14]=[CH:13][C:12]([C@H:9]5[CH2:8][CH2:7][C@H:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:11][CH2:10]5)=[CH:17][CH:16]=4)=[CH:23][CH:22]=3)=[O:25])[CH2:40][CH2:41]2)=[CH:32][CH:31]=1)[CH2:28][CH3:29]

Participants

5

Reactant 2

HCID 178439125HCID 178439125, compoundHCID 178444274HCID 178444274, compound

Product 1

HCID 178444280HCID 178444280, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1049PyridineSolvent

Conditions

Temperature
65 °C

Procedure

The crude 4'-(trans-4-pentylcyclohexyl)-4-biphenylcarboxylic acid chloride obtained was dissolved in 40 ml of benzene and then added dropwise to a solution of 0.90 g of trans-4-(p-propylphenyl)cyclohexanol in 20 ml of pyridine. The mixture was stirred at a bath temperature of 65° C. overnight, then poured into ice-water and extracted with diethyl ether. The extract was washed four times with 25 ml of 3N hydrochloric acid each time, then washed with 25 ml of 2N sodium carbonate solution and several times with water, dried over sodium sulphate and concentrated. The crude 4'-(trans-4-pentylcyclohexyl)-4-biphenylcarboxylic acid trans-4-(p-propylphenyl)cyclohexyl ester obtained was recrystallized once from ethanol containing a small amount of ethyl acetate and once from ethyl acetate. Yield 1.1 g; m.p. (C-S) 131.2° C.; phase transition S-N 143.3° C.; cl.p. (N-I) 337.5° C.

Workup

  1. extractionextracted with diethyl ether
  2. washThe extract was washed four times with 25 ml of 3N hydrochloric acid each time
  3. washwashed with 25 ml of 2N sodium carbonate solution and several times with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c02415fc8e2f44ba80ccf2c0f125606d
Source dataset
uspto-grants-1985_07
Patent number
US04526704

Reaction notes

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