Methanol → Methyl 3-chloro-4-isopropoxybenzoate

HRID 1785074Notes

Reaction equation

HRID 1785074 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, I H) 7.89 (dd, J=8.7, 2.1 Hz, 1H) 6.93 (d, J=8.6 Hz, 1H) 4.66 (qq, J=6.1 Hz, 1H) 3.88 (s, 3 H) 1.41 (d, J=6.1 Hz, 6H). 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-0a30d3f277fd4fedbbdb5f96906d6dfe
Source dataset
uspto-grants-2009_03
Patent number
US07504413B2

Reaction notes

Loading…