Hydrochloric Acid → 4-(Methylthio)-o-anisic acid

HRID 452444Notes

Reaction equation

[OH-].[Na+].BrBr.[CH3:5][O:6][C:7]1[CH:12]=[C:11]([S:13][CH3:14])[CH:10]=[CH:9][C:8]=1[C:15](=[O:17])C.[O-:18]S([O-])=O.[Na+].[Na+].Cl>O.O1CCOCC1>[CH3:5][O:6][C:7]1[CH:12]=[C:11]([S:13][CH3:14])[CH:10]=[CH:9][C:8]=1[C:15]([OH:17])=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodiumhydroxide (11.0 g, 275 mmol) was dissolved in water (70 ml) and cooled to 0° C. Bromine (3.5 ml, 68.7 mmol) was added, and after 15 min a cold solution of 1-[2-methoxy-4-(methylthio)phenyl]ethanone in dioxane (140 ml) was added dropwise during 20 min. The reaction mixture was stirred at 0° C. for 2.5 h. Na2SO3 (10 g dissolved in 50 ml water) was added and after 10 min the reaction mixture was acidified with an aqueous HCl (10%). The aqueous phase was extracted with EtOAc and the combined organic phases were dried (Na2SO4) and evaporated under reduced pressure to give an oil (5.7 g) of the title compound. Some sulfoxide and sulfonyl compound are also observed. 1H-NMR (400 MHz, MeOH): δ 7.77 (1H, d, J 8.4 Hz), δ 6.91 (1H, s), δ 6.84 (1H, dd, J1 8.0 Hz, J2 1.2 Hz), δ 3.96 (3H, s), δ 2.53 (3H, s).

Workup

extractionThe aqueous phase was extracted with EtOAc
dry with materialthe combined organic phases were dried (Na2SO4)
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-539b0345d35b4219a6d1e3af349b7b17
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492372B2

Reaction notes

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