4-Methoxybenzyl alcohol → HCID 11042776, compound

HRID 628167Notes

Reaction equation

HRID 628167 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+]>CC#N.CN(C1C=CN=CC=1)C.O>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][O:17][C:4](=[O:5])[CH2:3][CH2:2][C:1]([OH:6])=[O:7])=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 77384-Methoxybenzyl alcoholHCID 7922Succinic anhydrideHCID 10340Sodium Carbonate

Product 1

HCID 11042776HCID 11042776, compoundYield 88.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of succinic anhydride (10 g, 0.1 mol) in CH3CN (200 mL) were added (4-methoxyphenyl)methanol (69.0 g, 0.5 mol) and DMAP (12.2 g, 0.1 mol). The reaction mixture was stirred for 3 h at about 30° C. and then diluted with water (700 mL) The resulting mixture was adjusted to pH=10 with saturated Na2CO3 solution and washed with ethyl acetate (300 mL×4) to remove an excess of (4-methoxyphenyl)methanol. The aqueous phase was adjusted to pH=2 with saturated citric acid solution and then extracted with ethyl acetate (200 mL×2). The combined extracts were dried over anhydrous Na2SO4 and concentrated to give product (21.0 g, 88% yield) as a white solid.

Workup

  1. washwashed with ethyl acetate (300 mL×4)
  2. customto remove an excess of (4-methoxyphenyl)methanol
  3. extractionextracted with ethyl acetate (200 mL×2)
  4. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-316bb01aa900447d8924fb1c1c953388
Source dataset
uspto-grants-2016_04
Patent number
US09309283B2

Reaction notes

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