Dichloromethane → M-METHOXYBENZYL ACETATE

HRID 222459Notes

Reaction equation

HRID 222459 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][OH:10])[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.ClCCl.[C:21](OC(=O)C)(=[O:23])[CH3:22]>CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[CH2:9][O:10][C:21](=[O:23])[CH3:22]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 814373-Methoxybenzyl alcohol

Product 1

HCID 586565M-METHOXYBENZYL ACETATE

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3-methoxy-phenyl)-methanol (14.15 g, 102.4 mmol) and triethylamine (32.8 mL, 235.6 mmol) in dry dichloromethane (45 mL) dimethylaminopyridine (1.3 g, 10.2 mmol) and acetic anhydride (11.1 mL, 118.0 mmol) was added at 0° C. and the reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was diluted with EtOAc and washed with 1N HCl solution. The organic solution was dried over Na2SO4, evaporated in vacuo and purified by column chromatography (ethyl acetate:hexane; 5:95) to give the acetic acid 3-methoxy-benzyl ester as a slightly yellow oil (17.84 g, 96%). 1H NMR (CDCl3, 400 MHz) 2.08 (s, 3H), 3.78 (s, 3H), 5.06 (s, 2H), 6.85 (d, J=8.0 Hz, 1H), 6.89 (s, 1H), 6.92 (d, J=8.0 Hz, 1H), 7.25 (t, J=8.0 Hz, 1H), 13C NMR (CDCl3, 100 MHz) 20.6, 54.8, 65.7, 113.30, 113.32, 120.0, 129.2, 137.1, 159.4, 170.4.

Workup

  1. washwashed with 1N HCl solution
  2. dry with materialThe organic solution was dried over Na2SO4
  3. customevaporated in vacuo
  4. custompurified by column chromatography (ethyl acetate:hexane; 5:95)

Sources & evidence

ORD record
ord-73ed89f76028481cb60b2614f99d7f70
Source dataset
uspto-grants-2012_06
Patent number
US08207216B2

Reaction notes

Loading…