Benzoyl chloride → HCID 20252446, compound

HRID 638508Notes

Reaction equation

HRID 638508 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:26]=[CH:25][C:6]([O:7][C:8]2[CH:24]=[CH:23][C:11]([O:12][CH:13]([CH3:22])[CH:14]([OH:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]([F:27])([F:28])[C:3]1[CH:4]=[CH:5][C:6]([O:7][C:8]2[CH:24]=[CH:23][C:11]([O:12][CH:13]([CH3:22])[CH:14]([O:21][C:29](=[O:36])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][CH:9]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 12856783Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-hydroxypentanoate

Product 1

HCID 20252446HCID 20252446, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.5 g of ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-hydroxypentanoate were refluxed with 1.2 min. of benzoyl chloride in 60 ml of methylene chloride in the presence of 1.3 ml of triethylamine for 1(1/2) hours. The product was diluted with methylene chloride washed with water, 1M HCl and brine and dried over MgSO4. The product was purified by silica gel chromatography (total yield 92%) and was identified as a mixture of two stereoisomers of the above ethyl benzoyloxypentanoate.

Workup

  1. washwashed with water, 1M HCl and brine
  2. dry with materialdried over MgSO4
  3. customThe product was purified by silica gel chromatography (total yield 92%)
  4. additionwas identified as a mixture of two stereoisomers of the above ethyl benzoyloxypentanoate

Sources & evidence

ORD record
ord-7f770c58509143f59f8ac455aef33be7
Source dataset
uspto-grants-1985_12
Patent number
US04561882

Reaction notes

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