Triethylamine → 2-Propenoic acid, 2-methyl-, 6-(hydroxymethyl)-2-naphthalenyl ester

HRID 393133Notes

Reaction equation

HRID 393133 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([OH:13])[CH:7]=[CH:6]2.C(N(CC)CC)C.[C:21](Cl)(=[O:25])[C:22]([CH3:24])=[CH2:23]>ClCCl>[C:21]([O:13][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([CH2:2][OH:1])[CH:4]=2)[CH:9]=1)(=[O:25])[C:22]([CH3:24])=[CH2:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 113327606-(Hydroxymethyl)naphthalen-2-ol

Product 1

HCID 218953582-Propenoic acid, 2-methyl-, 6-(hydroxymethyl)-2-naphthalenyl esterYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

To a 3-necked, 500-mL round bottomed flask equipped with a digital thermometer, 50-mL constant-pressure addition funnel with a nitrogen inlet and a magnetic stir bar was added 25 g (0.14 mol) of 6-hydroxymethyl-2-naphthol, 200 mL of dichloromethane and 14.5 g (0.14 mol) of triethylamine. The addition funnel was charged with a solution of 14.9 g (0.15 mol) of methacryloyl chloride in 30 mL of dichloromethane. The flask was cooled to 5° C. and the acid chloride added slowly dropwise while maintaining a temperature of less than 10° C. The reaction mixture was stirred at room temperature overnight after which it was washed with water and brine, dried over MgSO4, evaporated and the residue chromatographed on silica gel with 35% ethyl acetate in hexane. The fractions containing the pure product were combined and evaporated to yield 22 g (65%) of the title compound as an off-white solid. Approximately 8 g of starting material can be recovered from the column by increasing the percentage of ethyl acetate in the mobile phase.

Workup

  1. customTo a 3-necked, 500-mL round bottomed flask equipped with a digital thermometer, 50-mL constant-pressure addition funnel with a nitrogen inlet and a magnetic stir bar
  2. temperaturewhile maintaining a temperature of less than 10° C
  3. washwas washed with water and brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customthe residue chromatographed on silica gel with 35% ethyl acetate in hexane
  7. additionThe fractions containing the pure product
  8. customevaporated

Sources & evidence

ORD record
ord-c43d5b23c624448ba33ccdc9cb3effc4
Source dataset
uspto-grants-2004_10
Patent number
US06806026B2

Reaction notes

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