p-Tolylacetic acid → Chloromethyl p-Methylphenylacetate

HRID 1496796Notes

Reaction equation

HRID 1496796 reaction equation
[C:1]([O:10][CH2:11][Cl:12])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH3:13]C1C=CC(CC(O)=O)=CC=1.C(=O)([O-])O.[Na+].ClCOS(Cl)(=O)=O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O.ClCCl.ClCCl>[CH3:13][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:1]([O:10][CH2:11][Cl:12])=[O:9])=[CH:4][CH:5]=1

Participants

8

Reactant 4

HCID 248474p-Tolylacetic acidHCID 516892Sodium BicarbonateHCID 525231Chloromethyl octanoateHCID 2733556Chloromethyl chlorosulfate

Product 1

HCID 117818026Chloromethyl p-MethylphenylacetateYield 80%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolventHCID 21908982Water methylene chlorideSolvent

Procedure

A similar procedure (Harada, N. et al. Synth. Commun. 1995, 25, 767-772) to that described for the preparation of 43 was followed using 4-methylphenylacetic acid (2.27 g, 15.15 mmol), sodium hydrogen carbonate (5.09 g, 60.6 mmol) and tetra-n-butylammonium hydrogen sulfate (0.51 g, 1.52 mmol) in water-dichloromethane (62.5 mL, 1:1 v/v) and chloromethylchlorosulfate (2.50 g, 15.15 mmol) in dichloromethane (7.5 mL), at room temperature for 18 h. Purification by flash chromatography (hexane/ethyl acetate 9:1) afforded 322 as a colourless oil (2.42 g, 12.18 mmol, 80%).

Workup

  1. customPurification by flash chromatography (hexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-b7f9cfc63a3146be8823fd64fc5f43a9
Source dataset
uspto-grants-2015_12
Patent number
US09198420B2

Reaction notes

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