Formaldehyde → chloromethyl 4-methoxybenzoate

HRID 1496794Notes

Reaction equation

HRID 1496794 reaction equation
[C:1]([O:7][CH2:8][Cl:9])(=[O:6])[C:2](C)([CH3:4])[CH3:3].C(Cl)(=O)C1C=[CH:15][C:14]([O:17][CH3:18])=[CH:13]C=1.C=O>[Cl-].[Zn+2].[Cl-]>[CH3:18][O:17][C:14]1[CH:15]=[CH:4][C:2]([C:1]([O:7][CH2:8][Cl:9])=[O:6])=[CH:3][CH:13]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 7477p-Anisoyl chlorideHCID 87885Chloromethyl pivalate

Product 1

HCID 242190chloromethyl 4-methoxybenzoateYield 12%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

A similar procedure (Iyer, R. P. et al. Synth. Commun. 1995, 25, 2739-2749) to that described for the preparation of 41 was followed using p-anisoyl chloride (5.0 g, 29.4 mmol), paraformaldehyde (883 mg, 29.4 mmol) and zinc chloride (31 mg, 0.22 mmol), at 80° C. for 16 h. Purification by flash chromatography (hexane/ethyl acetate 4:1) afforded chloromethyl p-methoxybenzoate (48) as a yellow oil (0.74 g, 3.69 mmol, 12%). 1H NMR (300 MHz, CDCl3) δ 3.87 (3H, s, OMe), 5.94 (2H, s, CH2), 6.92-6.96 (2H, m, Ar), 8.01-8.06 (2H, m, Ar).

Workup

  1. customPurification by flash chromatography (hexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-0c900c25e62f42feb8cfc5073dd51976
Source dataset
uspto-grants-2015_12
Patent number
US09198420B2

Reaction notes

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