Boron trifluoride etherate → 3-Benzylmercapto-4-carbomethoxy benzyl alcohol

HRID 2072302Notes

Reaction equation

HRID 2072302 reaction equation
B(F)(F)F.CCOCC.[CH2:10]([S:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[C:27]([O:29][CH3:30])=[O:28])[C:21](O)=[O:22])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O1CCCC1.[BH4-].[Na+].Cl.O>[CH2:10]([S:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[C:27]([O:29][CH3:30])=[O:28])[CH2:21][OH:22])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 2

HCID 8000Boron trifluoride etherateHCID 541082583-Benzylmercapto-4-carbomethoxy benzoic acid

Product 1

HCID 544090483-Benzylmercapto-4-carbomethoxy benzyl alcoholYield 65.2%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 4311764Sodium borohydrideSolvent

Procedure

28 ml of boron trifluoride etherate is added to a suspension of 46 g of crude 3-benzylmercapto-4-carbomethoxy benzoic acid in 750 ml of anhydrous tetrahydrofuran and 7 g of sodium borohydride. The reaction mixture is stirred for 3-4 hours at room temperature, then diluted with about 20 ml of 2N hydrochloric acid and 500 ml of water. The product obtained is extracted with ether and the ether extract is washed with water and saturated sodium chloride solution, dried over sodium sulfate and evaporated to dryness. Crystallization from ethyl acetate:hexane (1:2) yielded 28.6 g of 3-benzylmercapto-4-carbomethoxy benzyl alcohol having a melting point of 89.5°-92° C.

Workup

  1. customThe product obtained
  2. extractionis extracted with ether
  3. extractionthe ether extract
  4. washis washed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customCrystallization from ethyl acetate:hexane (1:2)

Sources & evidence

ORD record
ord-ea52d62c84174c999e6a506d1179c345
Source dataset
uspto-grants-1977_09
Patent number
US04051148

Reaction notes

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