Dichloromethane → Ethyl 2,3-dichloro-4-(4'-hydroxybenzyl)phenoxyacetate

HRID 2166844Notes

Reaction equation

HRID 2166844 reaction equation
FC(F)(F)C(O)=O.[BH4-].[Na+].[Cl:10][C:11]1[C:23]([Cl:24])=[C:22]([C:25](=O)[C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)[CH:21]=[CH:20][C:12]=1[O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(Cl)Cl>O>[Cl:10][C:11]1[C:23]([Cl:24])=[C:22]([CH2:25][C:26]2[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=2)[CH:21]=[CH:20][C:12]=1[O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydride2×HCID 12854007Ethyl 2,3-Dichloro-4-(4'-hydroxybenzoyl)phenoxyacetate

Product 1

HCID 13145653Ethyl 2,3-dichloro-4-(4'-hydroxybenzyl)phenoxyacetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To trifluoroacetic acid (50 ml.) under a nitrogen atmosphere was added 2.27 g. (0.06 mole) of NaBH4 pellets over a period of 30 minutes at 5°. A solution of ethyl 2,3-dichloro-4-(4'-hydroxybenzoyl)phenoxyacetate (prepared as described in Example 1) (3 g., 0.0081 mole) in 30 ml. of methylene chloride was added dropwise at 15°-20° over a period of 20 minutes. The reaction mixture was stirred overnight at room temperature while the NaBH4 pellets slowly dissolved. At this time the reaction mixture was poured into water and the resulting solution extracted with methylene chloride. The organic extract was washed with aqueous NaCL and dried over MgSO4. Evaporation of the methylene chloride furnished a residue which was chromatographed on a silica gel column eluting with increasing amounts of methanol (MeOH) in CH2Cl2. There was obtained 2 g. of white solid, m.p. 102°-103°.

Workup

  1. dissolutionslowly dissolved
  2. extractionthe resulting solution extracted with methylene chloride
  3. extractionThe organic extract
  4. washwas washed with aqueous NaCL
  5. dry with materialdried over MgSO4
  6. customEvaporation of the methylene chloride
  7. customfurnished a residue which
  8. customwas chromatographed on a silica gel column
  9. washeluting with increasing amounts of methanol (MeOH) in CH2Cl2
  10. customThere was obtained 2 g

Sources & evidence

ORD record
ord-e458709b3e71419db3d894573d878321
Source dataset
uspto-grants-1983_06
Patent number
US04389416

Reaction notes

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