Acetyl chloride → alpha-Acetoxy-3,4,5-trimethoxyphenyl-acetic acid

HRID 1666297Notes

Reaction equation

HRID 1666297 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([O:16][CH3:17])[C:13]=1[O:14][CH3:15])[CH:6]([OH:10])[C:7]([OH:9])=[O:8].[C:18](Cl)(=[O:20])[CH3:19]>>[C:18]([O:10][CH:6]([C:5]1[CH:11]=[C:12]([O:16][CH3:17])[C:13]([O:14][CH3:15])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:7]([OH:9])=[O:8])(=[O:20])[CH3:19]

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 139030963,4,5-Trimethoxymandelic acid

Product 1

HCID 67081678alpha-Acetoxy-3,4,5-trimethoxyphenyl-acetic acid

Procedure

3,4,5-Trimethoxymandelic acid (80.5 g) was treated with acetyl chloride (150 ml) at room temperature for three hours. The clear solution was concentrated to dryness under vacuum, and the oily residue was crystallized from toluene (280 ml) giving pure α-acetoxy-3,4,5-trimethoxyphenylacetic acid (80.9 g), m.p. 135-139° C.

Workup

  1. concentrationThe clear solution was concentrated to dryness under vacuum
  2. customthe oily residue was crystallized from toluene (280 ml)

Sources & evidence

ORD record
ord-a59961e20d414f499f2b7ec6ebbb983a
Source dataset
uspto-grants-2011_10
Patent number
US08044067B2

Reaction notes

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