Acetaldehyde → 1-Chloroethyl-2,2-dimethyl-3-(phenylmethoxy)propanoate

HRID 1919416Notes

Reaction equation

HRID 1919416 reaction equation
[CH3:1][C:2]([CH3:15])([CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3](Cl)=[O:4].[CH:16](=[O:18])[CH3:17].[Cl:19]CCl>[Cl-].[Zn+2].[Cl-]>[Cl:19][CH:16]([O:18][C:3](=[O:4])[C:2]([CH3:1])([CH3:15])[CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:17]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 6344DichloromethaneHCID 54421608HCID 54421608, compound

Product 1

HCID 674990361-Chloroethyl-2,2-dimethyl-3-(phenylmethoxy)propanoateYield 5%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

Following the general procedure for the synthesis of 1-chloroalkyl carboxylic esters of Description 21, 3.7 g (16.5 mmol) of 2,2-dimethyl-3-(phenylmethoxy)propanoyl chloride (26c) was reacted with 1.4 mL (1.1 g, 25 mmol) of acetaldehyde in 70 mL of anhydrous dichloromethane (DCM) in the presence of 0.25 g (1.8 mmol) of zinc chloride (ZnCl2). After work-up and isolation, the product was further purified by silica gel column chromatography using methyl tert-butyl ether (MTBE) and n-heptane (Hptn) mixtures as eluent (MTBE/Hptn=1:9) to provide 0.21 g (5% yield) of the title compound (26) as a yellow oil. Rf=0.24 (MTBE/Hptn=1:9). 1H NMR (400 MHz, CDCl3): δ=1.17 (s, 6H), 1.44 (d, J=5.6 Hz, 3H), 3.54 (s, 2H), 4.50 (s, 2H), 6.87 (q, J=5.6 Hz, 1H), 7.26-7.33 (m, 5H) ppm. The analytical data was consistent with the proposed structure.

Workup

  1. customAfter work-up and isolation, the product was further purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2b14b537c9ab461c828de6813bd33e62
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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