Pyridine → Acetoxy-(4-acetoxy-3-ethoxyphenyl)-acetic acid

HRID 1013564

Reaction equation

HRID 1013564 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:11]([OH:15])[C:12]([OH:14])=[O:13])[CH:7]=[CH:8][C:9]=1[OH:10])[CH3:2].N1C=CC=CC=1.[C:22](OC(=O)C)(=[O:24])[CH3:23].[CH2:29]([O:31]CC)[CH3:30]>C(Cl)Cl>[C:22]([O:15][CH:11]([C:6]1[CH:7]=[CH:8][C:9]([O:10][C:29](=[O:31])[CH3:30])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1)[C:12]([OH:14])=[O:13])(=[O:24])[CH3:23]

Participants

6

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 1937923-Ethoxy-4-hydroxymandelic acid

Product 1

HCID 20778781Acetoxy-(4-acetoxy-3-ethoxyphenyl)-acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Intermediate 2 (45.0 g, 0.212 mol, 1 eq.) was dissolved in DCM (225 mL), pyridine (80 mL, 0.989 mol, 6 eq.) was added and the mixture was cooled in an ice bath under nitrogen. Acetic anhydride (100 mL, 1.06 mol, 4 eq.) was added slowly via addition funnel. The mixture was stirred (−3 hr) until reaction was complete and then diluted with diethyl ether (500 mL) and washed with 1N HCl (4×250 mL). The mixture was extracted into 8% sodium bicarbonate solution (4×80 mL), acidified to ˜pH 4 with 6N HCl, and the product extracted into diethyl ether, giving 41.1 g of intermediate 3 as a white crystalline solid.

Workup

  1. temperaturethe mixture was cooled in an ice bath under nitrogen
  2. customuntil reaction
  3. washwashed with 1N HCl (4×250 mL)
  4. extractionThe mixture was extracted into 8% sodium bicarbonate solution (4×80 mL)
  5. extractionthe product extracted into diethyl ether

Sources & evidence

ORD record
ord-916302b39ebb4e6a9cf9a4e069260bbf
Source dataset
uspto-grants-2011_07
Patent number
US07981931B2

Linked notes

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