Toluene → 2,2-dimethoxyethyl (S)-6-methoxy-alpha-methyl-2-naphthaleneacetate

HRID 844514Notes

Reaction equation

HRID 844514 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][OH:5].CCN(CC)CC.C1(C)C=CC=CC=1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[CH:30]=[C:29]([C@H:34]([CH3:38])[C:35](Cl)=[O:36])[CH:28]=[CH:27]2>CN(C1C=CN=CC=1)C.O>[CH3:22][O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[CH:30]=[C:29]([C@H:34]([CH3:38])[C:35]([O:5][CH2:4][CH:3]([O:6][CH3:7])[O:2][CH3:1])=[O:36])[CH:28]=[CH:27]2

Participants

7

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 5423812,2-DimethoxyethanolHCID 54916922-(6-Methoxynaphthalen-2-yl)propanoyl chloride

Product 1

HCID 867580112,2-dimethoxyethyl (S)-6-methoxy-alpha-methyl-2-naphthaleneacetateYield 89.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

2,2-Dimethoxyethanol (8.12 g), Et3N (8.99 g), DMAP (80 mg) and toluene (71 mL) are combined and stirred at room temperature. (S)-6-Methoxy-α-methyl-2-naphthaleneacetyl chloride (18.42 g) is added in portions over a period of 8 minutes. The resulting slurry is agitated (35-40° C.) until the reaction is judged to be complete. To the reaction mixture is added water (80 mL) and the phases are separated. The toluene phase is washed with saturated sodium bicarbonate (40 mL) and water (40 mL) and concentrated. Dichloromethane (20 mL) is added and the vacuum evaporation is repeated to produce 21.20 g of 2,2-dimethoxyethyl (S)-6-methoxy-α-methyl-2-naphthaleneacetate.

Workup

  1. stirringThe resulting slurry is agitated (35-40° C.) until the reaction
  2. customthe phases are separated
  3. washThe toluene phase is washed with saturated sodium bicarbonate (40 mL) and water (40 mL)
  4. concentrationconcentrated
  5. additionDichloromethane (20 mL) is added
  6. customthe vacuum evaporation

Sources & evidence

ORD record
ord-821c55ec22a94befadea3375353b0db2
Source dataset
uspto-grants-2002_04
Patent number
US06380388B1

Reaction notes

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