Methanol → Methyl 3-chloro-4-isopropoxybenzoate

HRID 1621256Notes

Reaction equation

HRID 1621256 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) ppm 8.04 (d, J=2.3 Hz, 1H) 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, 3H) 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-d0a788f6ed80474896fc6f6615e8663b
Source dataset
uspto-grants-2014_07
Patent number
US08772507B2

Reaction notes

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