Cyclohexane → Methyl 3,4,5-tris(octadecyloxy)cyclohexylcarboxylate

HRID 537611Notes

Reaction equation

HRID 537611 reaction equation
[CH2:1]([O:19][C:20]1[CH:21]=[C:22]([CH:27]=[C:28]([O:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH3:67])[C:29]=1[O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[C:23]([O:25][CH3:26])=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C1CCCCC1>[C].[Rh].O1CCCC1>[CH2:1]([O:19][CH:20]1[CH:29]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[CH:28]([O:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH3:67])[CH2:27][CH:22]([C:23]([O:25][CH3:26])=[O:24])[CH2:21]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 8078CyclohexaneHCID 11320558Methyl 3,4,5-tris(octadecyloxy)benzoate

Product 1

HCID 86654892Methyl 3,4,5-tris(octadecyloxy)cyclohexylcarboxylateYield 82%

Reagents, catalysts & solvents 2

HCID 178503043HCID 178503043, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To methyl 3,4,5-tris(octadecyloxy)benzoate (1 g, 10.6 mmol) was added cyclohexane, 5% rhodium-carbon (0.8 g) was added, and hydrogenation was performed at 80° C., 10 atm. Tetrahydrofuran (10 ml) was added, and the catalyst was filtered off. The filtrate was concentrated, methanol (8 ml) was added, and the mixture was stirred. The precipitate was collected by filtration and dried to give methyl 3,4,5-tris(octadecyloxy)cyclohexylcarboxylate (820 mg, 0.87 mmol, 82%).

Workup

  1. additionwas added
  2. customwas performed at 80° C.
  3. filtrationthe catalyst was filtered off
  4. concentrationThe filtrate was concentrated
  5. additionmethanol (8 ml) was added
  6. filtrationThe precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-5779910a11b04d449aa0a8a286ac3585
Source dataset
uspto-grants-2014_10
Patent number
US08859732B2

Reaction notes

Loading…