Methanol → Methyl 3-chloro-4-isopropoxybenzoate

HRID 730378Notes

Reaction equation

HRID 730378 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13])[C:5]([OH:7])=[O:6].O=S(Cl)Cl.[CH3:19]O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13])[C:5]([O:7][CH3:19])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 225977283-Chloro-4-(propan-2-yloxy)benzoic acid

Product 1

HCID 22597811Methyl 3-chloro-4-isopropoxybenzoate

Procedure

A solution of 3-chloro-4-[(1-methylethyl)oxy]benzoic acid (1.00 g, 4.66 mmol) in methanol (10.0 mL) was treated with SOCl2 (0.68 mL, 9.32 mmol). After stirring overnight at ambient temperature, the solution was concentrated in vacuo and taken on without purification. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.04 (d, J=2.3 Hz, 1 H) 7.89 (dd, J=8.7, 2.1 Hz, 1 H) 6.93 (d, J=8.6 Hz, 1 H) 4.66 (qq, J=6.1 Hz, 1 H) 3.88 (s, 3 H) 1.41 (d, J=6.1 Hz, 6 H). MS(ES+) m/e 229 [M+H]+.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customtaken on without purification

Sources & evidence

ORD record
ord-521815ff515a4a4b838c8e913d61fa6a
Source dataset
uspto-grants-2009_09
Patent number
US07582668B2

Reaction notes

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