Cyclohexanecarbonyl chloride → HCID 53815786, compound

HRID 2050104Notes

Reaction equation

HRID 2050104 reaction equation
[CH3:1][C:2]([CH3:46])=[CH:3][CH2:4][CH2:5]/[C:6](/[CH3:45])=[CH:7]/[CH2:8][CH2:9]/[C:10](/[CH3:44])=[CH:11]/[CH2:12][CH2:13]/[C:14](/[CH3:43])=[CH:15]/[CH2:16][CH2:17]/[C:18](/[CH3:42])=[CH:19]/[CH2:20][CH2:21]/[C:22](/[CH3:41])=[CH:23]/[CH2:24][CH2:25]/[C:26](/[CH3:40])=[CH:27]/[CH2:28][CH2:29]/[C:30](/[CH3:39])=[CH:31]/[CH2:32][CH2:33]/[C:34](/[CH3:38])=[CH:35]/[CH2:36][OH:37].[CH:47]1([C:53](Cl)=[O:54])[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]1>N1C=CC=CC=1.CCCCCC>[CH:47]1([C:53]([O:37][CH2:36][CH:35]=[C:34]([CH3:38])[CH2:33][CH2:32][CH:31]=[C:30]([CH3:39])[CH2:29][CH2:28][CH:27]=[C:26]([CH3:40])[CH2:25][CH2:24][CH:23]=[C:22]([CH3:41])[CH2:21][CH2:20][CH:19]=[C:18]([CH3:42])[CH2:17][CH2:16][CH:15]=[C:14]([CH3:43])[CH2:13][CH2:12][CH:11]=[C:10]([CH3:44])[CH2:9][CH2:8][CH:7]=[C:6]([CH3:45])[CH2:5][CH2:4][CH:3]=[C:2]([CH3:46])[CH2:1][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:54])[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]1

Participants

5

Reactant 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 5477212Solanesol

Product 1

HCID 53815786HCID 53815786, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 8058HexaneSolvent

Procedure

10 Grams of solanesol were dissolved in 50 ml of pyridine and the solution was added dropwise with of 15% solution of 4.6 g of cyclohexylcarboxylic acid chloride in pyridine over 30 minutes. After completion of the addition, the mixture was stirred at room temperature for two hours to complete the reaction. Then, the reaction product was diluted with n-hexane, washed with water and concentrated. The concentrate was purified by chromatography with 80 g of silica gel in n-hexane/benzene solvent mixture as elution solvent to obtain the final product as a white solid (m.p. 34.0°-35.0° C.). Yield: 6.2 g.

Workup

  1. additionAfter completion of the addition
  2. customthe reaction
  3. washwashed with water
  4. concentrationconcentrated
  5. customThe concentrate was purified by chromatography with 80 g of silica gel in n-hexane/benzene solvent mixture as elution solvent

Sources & evidence

ORD record
ord-b6cd2644efc041649ce1df5c33587123
Source dataset
uspto-grants-1980_04
Patent number
US04199587

Reaction notes

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