Hydrochloric Acid → HCID 9903861, compound

HRID 844827Notes

Reaction equation

HRID 844827 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH:11]=[O:12])[C:8]([CH3:13])=[CH:7][C:6]=1[S:14][C:15](=[O:19])[N:16]([CH3:18])[CH3:17])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+].C1(C)C=CC=CC=1.Cl>C1COCC1.O>[C:1]([C:5]1[CH:10]=[C:9]([CH2:11][OH:12])[C:8]([CH3:13])=[CH:7][C:6]=1[S:14][C:15](=[O:19])[N:16]([CH3:17])[CH3:18])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 4148881Lithium borohydrideHCID 9795669HCID 9795669, compound

Product 1

HCID 9903861HCID 9903861, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dimethylthiocarbamic acid S-(2-tert-butyl-4-formyl-5-methylphenyl) ester (4a) (6.0 gm, 21 mmol) was dissolved in THF and treated with lithium borohydride (0.8 gm) in portions. The mixture was cooled in an ice bath and stirring continued for 1.5 hours. Toluene (25 mL) and water (10 mL) were added followed by cautious addition of 37% hydrochloric acid (2.8 gm) to destroy excess borohydride and adjust the pH to 6.5. The aqueous layer was separated and the organic layer extracted with 1 N NaOH (2×10 mL) and water (10 mL) and concentrated to a solid. This was recrystallized from toluene and heptane and the crystals vacuum dried at 40° C. to give dimethylthiocarbamic acid S-(2-tert-butyl-4-hydroxymethyl-5-methylphenyl) ester (5a) (5.6 gm): mp: 135.9-136.4° C.; HPLC: 99.1%.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. customto destroy excess borohydride
  3. customThe aqueous layer was separated
  4. extractionthe organic layer extracted with 1 N NaOH (2×10 mL) and water (10 mL)
  5. concentrationconcentrated to a solid
  6. customThis was recrystallized from toluene and heptane
  7. customthe crystals vacuum dried at 40° C.

Sources & evidence

ORD record
ord-633a13c347de4b0590c7f7a2533b9e53
Source dataset
uspto-grants-2002_04
Patent number
US06380400B1

Reaction notes

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