Water → Methyl 4-(3-chloropropoxy)benzoate

HRID 359068Notes

Reaction equation

C(=O)([O-])[O-:2].[K+].[K+].Br[CH2:8][CH2:9][CH2:10][Cl:11].O.[C:13]([O:16][CH2:17]C)(=[O:15])[CH3:14].[CH3:19][CH2:20][CH2:21][CH2:22][CH2:23]C>CN(C=O)C>[Cl:11][CH2:10][CH2:9][CH2:8][O:2][C:21]1[CH:22]=[CH:23][C:14]([C:13]([O:16][CH3:17])=[O:15])=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

p-Methyl hydroxybenzoate (40 g) and potassium carbonate (54.5 g) in N,N-dimethylformaldehyde (200 ml) were heated with stirring at 100° C. for 1 hour, cooled to 40° C., and then, after adding 1-bromo-3-chloropropane (28.5 ml), the mixture was reacted at 60° C. for 2 hours. After cooling the reaction mixture, water and ethyl acetate were added thereto, and the mixture was separated into layers. The organic layer was washed with water 3 times, concentrated under reduced pressure. To the oily product thus obtained, a small amount of ethyl acetate and n-hexane were added. After the mixture was allowed to stand, the precipitated crystal was collected by filtration and the filtrate was again concentrated under reduced pressure to give the crystal of methy 4-(3-chloropropoxy)benzoate (56.92 g). mp. 52°-55° C.

Workup

temperaturecooled to 40° C.
customthe mixture was reacted at 60° C. for 2 hours
additionwere added
customthe mixture was separated into layers
washThe organic layer was washed with water 3 times
concentrationconcentrated under reduced pressure
customTo the oily product thus obtained
filtrationthe precipitated crystal was collected by filtration
concentrationthe filtrate was again concentrated under reduced pressure

Sources & evidence

ORD record: ord-862f544e516040858c89fe1ad9db7397
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04999378

Reaction notes

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