Water → 2-Chloro-4,5-dihydroxymandelic acid

HRID 1788824Notes

Reaction equation

HRID 1788824 reaction equation
S(Cl)([Cl:4])(=O)=O.[OH:6][C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][C:17]=1[OH:18])[CH:10]([OH:14])[C:11]([OH:13])=[O:12].O>C(O)(=O)C>[Cl:4][C:15]1[CH:16]=[C:17]([OH:18])[C:7]([OH:6])=[CH:8][C:9]=1[CH:10]([OH:14])[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 85782(+-)-3,4-Dihydroxymandelic acid

Product 1

HCID 201899772-Chloro-4,5-dihydroxymandelic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sulphuryl chloride (0.8 ml) was added to a solution of 3,4-dihydroxymandelic acid (1.84 g, 10 mmol) in warm acetic acid (20 ml). The mixture was stirred for two hours then poured into water and extracted with ethyl acetate (6×40 ml). The extracts were washed with saturated brine (50 ml), dried and evaporated to a crystalline mass (2.36 g) which was recrystallised from ethyl acetate-cyclohexane, 0.97 g, 44%, mp 177°, δ[(CD3)2SO] 5.15(1H, s, CH), 6.71 and 6.85(2H, 2×s, Ar), 8.4-9.8(3H, m, 2×OH, CO2H).

Workup

  1. extractionextracted with ethyl acetate (6×40 ml)
  2. washThe extracts were washed with saturated brine (50 ml)
  3. customdried
  4. customevaporated to a crystalline mass (2.36 g) which
  5. customwas recrystallised from ethyl acetate-cyclohexane, 0.97 g, 44%, mp 177°, δ[(CD3)2SO] 5.15(1H, s

Sources & evidence

ORD record
ord-7974117b850745ce99478a14fbf8fabe
Source dataset
uspto-grants-1987_08
Patent number
US04684639

Reaction notes

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