Phenylacetic Acid → Chloromethyl phenylacetate

HRID 1496795Notes

Reaction equation

HRID 1496795 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].C1(CC(O)=O)C=CC=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>[C:3]1([CH2:2][C:1]([O:10][CH2:11][Cl:12])=[O:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 999Phenylacetic AcidHCID 516892Sodium BicarbonateHCID 525231Chloromethyl octanoateHCID 2733556Chloromethyl chlorosulfate

Product 1

HCID 11286872Chloromethyl phenylacetateYield 31%

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 phenylacetic acid (4.50 g, 31.2 mmol), sodium hydrogen carbonate (10.48 g, 124.8 mmol) and tetra-n-butylammonium hydrogen sulfate (1.06 g, 3.12 mmol) in water-dichloromethane (125 mL, 1:1 v/v) and chloromethylchlorosulfate (5.15 g, 31.2 mmol) in dichloromethane (15 mL), at room temperature for 18 h. Purification by flash chromatography (hexane/ethyl acetate 9:1) afforded 49 as a yellow oil (1.81 g, 9.82 mmol, 31%).

Workup

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

Sources & evidence

ORD record
ord-4e47db7472554e41ab87214f2f327908
Source dataset
uspto-grants-2015_12
Patent number
US09198420B2

Reaction notes

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