Hydrochloric Acid → Methyl 4-hydroxy-8-methylthiochroman-7-carboxylate

HRID 1596761Notes

Reaction equation

HRID 1596761 reaction equation
[CH3:1][C:2]1[C:3]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][CH:5]=[C:6]2[C:11]=1[S:10][CH2:9][CH2:8][C:7]2=[O:12].[BH4-].[Na+].Cl>C(Cl)Cl.CO>[OH:12][CH:7]1[C:6]2[C:11](=[C:2]([CH3:1])[C:3]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][CH:5]=2)[S:10][CH2:9][CH2:8]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 15335227Methyl 8-methylthiochroman-4-one-7-carboxylate

Product 1

HCID 15335230Methyl 4-hydroxy-8-methylthiochroman-7-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

30 g (0.127 mol) of methyl 8-methylthiochroman-4-one-7-carboxylate are dissolved in a mixture of 120 ml of methylene chloride and 60 ml of methanol and the solution is cooled to 0-5° C. 2.4 g (0.064 mol) of sodium borohydride are then added a little at a time. Stirring is continued at this temperature for one hour. 200 ml of 2N hydrochloric acid are added to the reaction solution. This gives two phases. The organic phase is separated off and dried and the solvent is distilled off. The crude product is further reacted directly without further purification.

Workup

  1. customThis gives two phases
  2. customThe organic phase is separated off
  3. customdried
  4. distillationthe solvent is distilled off
  5. customThe crude product is further reacted directly without further purification

Sources & evidence

ORD record
ord-850fc334e08c471ba2434688b30e1147
Source dataset
uspto-grants-2001_09
Patent number
US06291682B1

Reaction notes

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