Reaction #2446099

Reaction equation

dichloromethane

1-naphthol

triethyl amine

naphthol

methacryloyl chloride

→

naphthalen-1-yl methacrylate

Yield 90.0%

Solvents

water

Conditions

Workup

1. 1
   DryingAn oven dried 250 mL 2 neck round bottom flask
2. 2
   Otherfitted with a dropping funnel and guard tube under inert atmosphere
3. 3
   workup.ADDITIONwas added slowly over a period of 15 min at −5° C
4. 4
   Temperatureto warm to room temperature
5. 5
   workup.STIRRINGstirred for another 2 h at room temperature
6. 6
   OtherReaction
7. 7
   OtherReaction mixture
8. 8
   workup.ADDITIONwas poured into a 500 mL
9. 9
   Otherseparating funnel
10. 10
    Washthe organic layer was washed with water and aq. Na2CO3 The organic layer
11. 11
    Washwere again washed with water
12. 12
    Dryingdried over anhydrous Na2SO4
13. 13
    OtherDCM was removed under reduced pressure

Procedure

An oven dried 250 mL 2 neck round bottom flask fitted with a dropping funnel and guard tube under inert atmosphere was charged with 100 mL of dry dichloromethane, 1-naphthol (1) (5.0 g, 34.6 mmol) and triethyl amine (7.0 g, 70.0 mmol). The flask was cooled to −5° C. (ice & water bath), methacryloyl chloride (2) (5.4 g, 52.0 mmol) was added slowly over a period of 15 min at −5° C. The reaction was stirred for 2 h at −5° C. and allow to warm to room temperature and stirred for another 2 h at room temperature. Reaction was monitored by TLC (until naphthol was absent). Reaction mixture was poured into a 500 mL separating funnel and the organic layer was washed with water and aq. Na2CO3 The organic layer were again washed with water and dried over anhydrous Na2SO4. DCM was removed under reduced pressure and the product was a viscous oil (compound 3) (6.61 g, yield 90%).

Source