HCID 13463460, compound → HCID 178444426, compound

HRID 1090605Notes

Reaction equation

HRID 1090605 reaction equation
[CH3:1][C@@H:2]([CH2:18][CH3:19])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1.[CH2:20]([C@H:25]1[CH2:30][CH2:29][C@H:28]([CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=2)[CH2:27][CH2:26]1)[CH2:21][CH2:22][CH2:23][CH3:24]>C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH2:20]([C@H:25]1[CH2:26][CH2:27][C@H:28]([CH2:31][CH2:32][C:33]2[CH:34]=[CH:35][C:36]([O:39][C:13](=[O:14])[C:12]3[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C@@H:2]([CH3:1])[CH2:18][CH3:19])=[CH:17][CH:16]=3)=[CH:37][CH:38]=2)[CH2:29][CH2:30]1)[CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 2

HCID 13463460HCID 13463460, compoundHCID 178444415HCID 178444415, compound

Product 1

HCID 178444426HCID 178444426, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

The crude (S)-4-(6-methyloctyloxy)benzoyl chloride obtained was dissolved in 20 ml of toluene and then added dropwise to a solution of 0.26 g of 4-[2-(trans-4-pentylcyclohexyl)ethyl]phenol in 2 ml of pyridine. The reaction mixture was stirred at room temperature 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 magnesium sulphate and concentrated. Chromatography of the residual oil on silica gel with toluene gave 0.2 g of (S)-4-(6-methyloctyloxy)benzoic acid 4-[2-(trans-4-pentylcyclohexyl)ethyl]phenyl ester. The product was recrystallized several times from ethanol until the phase transition temperatures were constant. M.p. (C-S) 58°, transition S-S*C 58.5° C., transition S*C -Ch 93° C., cl.p. (Ch-I) 140° 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 magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f0575a1069de4cd896ed67c3f35c0822
Source dataset
uspto-grants-1992_01
Patent number
US05082589

Reaction notes

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