Water → 2-Chloro-1-(2-methoxyphenyl)ethan-1-ol

HRID 66319Notes

Reaction equation

HRID 66319 reaction equation
CO[CH:3]([Cl:12])[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].O.[BH4-].[Na+].[O:16]1CCOC[CH2:17]1>>[Cl:12][CH2:3][CH:4]([OH:5])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=1[O:16][CH3:17]

Participants

5

Reactant 4

HCID 962WaterHCID 312751,4-DioxaneHCID 4311764Sodium borohydrideHCID 227549172-Methoxy-alpha-chloroacetophenone

Product 1

HCID 224917592-Chloro-1-(2-methoxyphenyl)ethan-1-ol

Procedure

4.55 g of 2-methoxy-α-chloroacetophenone are dissolved in 70 ml of dioxane, and 30 ml of water are added thereto. 1.5 g of sodium borohydride are added gradually to the solution at 10° to 20° C. Then, the mixture is stirred at room temperature for 3 hours. The reaction mixture is poured into ice-water. The aqueous mixture is extracted with benzene. Then, the extract is dried and evaporated to remove solvent. 3.7 g of α-chloromethyl-2-methoxybenzylalcohol are obtained as a crude oil.

Workup

  1. extractionThe aqueous mixture is extracted with benzene
  2. customThen, the extract is dried
  3. customevaporated
  4. customto remove solvent

Sources & evidence

ORD record
ord-4a82392bfe4844379133d7f0a6e677cb
Source dataset
uspto-grants-1978_12
Patent number
US04131686

Reaction notes

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