Hydrochloric Acid → 855382-76-2

HRID 1436857Notes

Reaction equation

HRID 1436857 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:11][C:12](O)=[O:13].[BH4-].[Na+].CS(O)(=O)=O.Cl>O1CCCC1.O>[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][OH:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6395Methanesulfonic AcidHCID 4311764Sodium borohydrideHCID 135308972-(2-Methyl-3-nitrophenyl)acetic acid

Product 1

HCID 11998857855382-76-2Yield 97.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
67.5 °C

Procedure

A solution of 2-Methyl-3-nitro phenylaceticacid (160 g) in Tetrahydrofuran (480 ml) is added to Sodium borohydride (75 g) and Tetrahydrofuran (160 ml). Further, Methanesulfonicacid (53 ml) is added to reaction mixture at ambient temperature and stirred at 60-75° C. until the completion of reaction. 3N Hydrochloric acid (384 ml) is added to reaction mixture followed by addition of water (1420 ml). Reaction mixture is extracted twice with Dichloro methane (1×800 ml and 1×400 ml) and organic layer is separated. The combined organic layer is washed with NaHCO3 solution and brine solution. Dichloromethane is distilled out under vacuum at 40-50° C. to obtain 2-Methyl-3-nitro phenyl ethyl alcohol as dark brown oil (˜145 g).

Workup

  1. customReaction mixture
  2. extractionis extracted twice with Dichloro methane (1×800 ml and 1×400 ml) and organic layer
  3. customis separated
  4. washThe combined organic layer is washed with NaHCO3 solution and brine solution
  5. distillationDichloromethane is distilled out under vacuum at 40-50° C.

Sources & evidence

ORD record
ord-2797b2052ee64da598fcd087089ebfd8
Source dataset
uspto-grants-2009_11
Patent number
US07619095B2

Reaction notes

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