Hydrochloric Acid → HCID 18443682, compound

HRID 1828804Notes

Reaction equation

HRID 1828804 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[C:11]([Cl:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([CH2:13][OH:14])=[C:11]([Cl:18])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 50979854-(Benzyloxy)-2-chlorobenzoic acid

Product 1

HCID 18443682HCID 18443682, compoundYield 104.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-benzyloxy-2-chlorobenzoic acid (788 mg) in tetrahydrofuran (7.9 ml) was added dropwise borane-dimethylsulfide complex (10.0M, 0.6 ml) at room temperature under a nitrogen atmosphere and the mixture was refluxed under heating for 2.5 hr. The reaction mixture was allowed to cool to room temperature, and 1N hydrochloric acid (1.5 ml) was carefully added dropwise. The mixture was stirred for 30 min. To the reaction mixture was added water and the resulting product was extracted 3 times with ethyl acetate. The organic layers were combined, washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated to give 4-benzyloxy-2-chlorobenzyl alcohol (778 mg) as a white powder.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 2.5 hr
  3. extractionthe resulting product was extracted 3 times with ethyl acetate
  4. washwashed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-36cdcb0dc4af4a2686cae0c922ac8c13
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

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