Water → Methyl 3-(3-methylphenylthio)propanoate

The reaction was repeated by cooling a solution of 15.7 grams (0.126 mole) of 3-methylbenzenethiol and 23.3 grams (0.139 mole) of methyl 3-bromopropanoate in about 140 mL of DMF in an ice water bath prior to the addition of 14.1 grams (0.139 mole) of triethylamine. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature where it stirred for an 18 hour period. The reaction mixture was then poured into 200 mL of water, and the mixture was extracted with three 200 mL portions of ethyl acetate. The combined extracts were washed with water, and then with three 50 mL portions of an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate, and the mixture was filtered. The filtrate was concentrated under reduced pressure to a residue, yielding 23.5 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

1. additionUpon completion of addition
2. extractionthe mixture was extracted with three 200 mL portions of ethyl acetate
3. washThe combined extracts were washed with water
4. dry with materialThe organic layer was dried with sodium sulfate
5. filtrationthe mixture was filtered
6. concentrationThe filtrate was concentrated under reduced pressure to a residue

ORD record

ord-c4adb40af1704f58a34909911823efdc

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07767667B2