Dichloromethane → Naphthyl methacrylate

HRID 2358917Notes

Reaction equation

HRID 2358917 reaction equation
ClCCl.[C:4]1([OH:14])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:22](Cl)(=[O:26])[C:23]([CH3:25])=[CH2:24]>O>[C:22]([O:14][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)(=[O:26])[C:23]([CH3:25])=[CH2:24]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 70051-Naphthol2×HCID 8471TriethylamineHCID 13528Methacryloyl chloride

Product 1

HCID 4064248Naphthyl methacrylateYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-5 °C

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%).

Workup

  1. dry with materialAn oven dried 250 mL 2 neck round bottom flask
  2. customfitted with a dropping funnel and guard tube under inert atmosphere
  3. additionwas added slowly over a period of 15 min at −5° C
  4. temperatureto warm to room temperature
  5. stirringstirred for another 2 h at room temperature
  6. customReaction
  7. customReaction mixture
  8. additionwas poured into a 500 mL
  9. customseparating funnel
  10. washthe organic layer was washed with water and aq. Na2CO3 The organic layer
  11. washwere again washed with water
  12. dry with materialdried over anhydrous Na2SO4
  13. customDCM was removed under reduced pressure

Sources & evidence

ORD record
ord-86167dd938714e4abe834d90aee04245
Source dataset
uspto-grants-2014_04
Patent number
US08685616B2

Reaction notes

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