Sodium Acetate → HCID 23692550, compound

HRID 32876Notes

Reaction equation

HRID 32876 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([O:13][CH3:14])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+:19]>CO>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C@H:9]([O:13][CH3:14])[C:10]([O-:12])=[O:11])=[CH:6][CH:7]=1.[Na+:19]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 11564639(2S)-3-(4-hydroxyphenyl)-2-methoxypropanoic acid

Product 1

HCID 23692550HCID 23692550, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

420 ml of the (S)-3-(4-hydroxyphenyl)-2-methoxypropionic acid solution from above are treated with stirring with a solution of 16.32 g of sodium acetate in 136 ml of methanol. After addition of seed crystals, the mixture is stirred for 12 h at room temperature. The precipitated product is filtered off and the filter cake is washed twice with 20 ml each of MIBK. The product is dried in vacuo at 50° C. in the course of 12 h. 30.2 g (34.8%) of sodium (S)-3-(4-hydroxyphenyl)-2-methoxypropionate are obtained. Optical purity ee=95-97%. Chemical purity >99%.

Workup

  1. additionAfter addition of seed crystals
  2. filtrationThe precipitated product is filtered off
  3. washthe filter cake is washed twice with 20 ml each of MIBK
  4. customThe product is dried in vacuo at 50° C. in the course of 12 h

Sources & evidence

ORD record
ord-ba239b96a02449e8bf964db5791c122d
Source dataset
uspto-grants-2008_09
Patent number
US07427691B2

Reaction notes

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