m-Chloroperbenzoic acid → 2-Chloro-3-methoxyphenol

3-Chloroperoxybenzoic acid (760 mg, 4.396 mmol) was added portionwise to a solution of 2-Chloro-3-Methoxybenzaldehyde (500 mg, 2.931 mmol) in dichloromethane (12 ml) and the mixture was stirred for 3 hours at room temperature. Further 3-chloroperoxybenzoic acid (760 mg, 4.396 mmol) was added and mixture allowed to stir for 18 hrs. The solution was diluted with 12 ml dichloromethane and washed with saturated sodium sulphite solution (15 ml) and saturated sodium hydrogen carbonate solution (15 ml). The organic layer was dried over sodium sulphate and concentrated in vacuo to a yellow gum. The residue was dissolved in methanol (12 ml), triethylamine (0.05 ml) was added and the mixture stirred for 18 hours at room temperature. The solution was concentrated in vacuo, dissolved in diethyl ether (20 ml) and extracted with 1N sodium hydroxide (20 ml). The aqueous layer was acidified to pH1 by dropwise addition of 2N hydrochloric acid and extracted with diethyl ether (2×25 ml). These combined organic layers were dried over sodium sulphate and concentrated in vacuo to afford the title compound as a brown gum in 70% yield, 325 mg.

1. stirringto stir for 18 hrs
2. washwashed with saturated sodium sulphite solution (15 ml) and saturated sodium hydrogen carbonate solution (15 ml)
3. dry with materialThe organic layer was dried over sodium sulphate
4. concentrationconcentrated in vacuo to a yellow gum
5. dissolutionThe residue was dissolved in methanol (12 ml)
6. additiontriethylamine (0.05 ml) was added
7. stirringthe mixture stirred for 18 hours at room temperature
8. concentrationThe solution was concentrated in vacuo
9. dissolutiondissolved in diethyl ether (20 ml)
10. extractionextracted with 1N sodium hydroxide (20 ml)
11. additionThe aqueous layer was acidified to pH1 by dropwise addition of 2N hydrochloric acid
12. extractionextracted with diethyl ether (2×25 ml)
13. dry with materialThese combined organic layers were dried over sodium sulphate
14. concentrationconcentrated in vacuo

ORD record

ord-27f4232a106f4213b66d16569e41505a

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08486992B2