Dichloromethane → HCID 19784616, compound

HRID 257151Notes

Reaction equation

HRID 257151 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:7][C:6]=1[CH:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:16]([OH:18])=[O:17])[CH:2]=[CH2:3].[CH2:25](O)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].ClCCl.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:7][C:6]=1[CH:15]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:16]([O:18][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH3:25])=[O:17])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8221Stearyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 19784608HCID 19784608, compound2×

Product 1

HCID 19784616HCID 19784616, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A solution of 3.24 g (10.0 mmol) of 2-(2-allyloxy-5-tert-butylphenyl)-2-phenylacetic acid (compound (105), Example 2) and 2.70 g (10.0 mmol) of stearyl alcohol (1-octadecanol) in 25 mol of dichloromethane is treated with 100 mg (0.82 mmol) of 4-dimethylaminopyridine and 2.20 g (10.7 mmol) of N,N'-dicyclohexylcarbodiimide, and the mixture is stirred for 60 hours at room temperature. The reaction mixture is filtered and concentrated on a vacuum rotary evaporator. Chromatography of the residue from silica gel using the diluent system dichloromethane/hexane=1:1 yields 4.0 g (69%) of stearyl 2-(2-allyloxy-5-tert-butylphenyl)-2-phenylacetate (compound (106), Table 1) as an oil.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated on a vacuum rotary evaporator

Sources & evidence

ORD record
ord-271d286a7ac74507a81a12a137bee09f
Source dataset
uspto-grants-1993_11
Patent number
US05260430

Reaction notes

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