2-Chloroethanol → Benzaldehyde, 4-(2-hydroxyethoxy)-

HRID 2260700Notes

Reaction equation

HRID 2260700 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].Cl[CH2:13][CH2:14][OH:15]>O>[OH:15][CH2:14][CH2:13][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 1264-HydroxybenzaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 89178Benzaldehyde, 4-(2-hydroxyethoxy)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-hydroxybenzaldehyde (45.5 g), sodium hydroxide (15 g) and 2-chloroethanol (30 g, 25 ml) was heated at reflux in water (200 ml) for 7 hours. The mixture was cooled and extracted with dichloromethane (200 ml). The dichloromethane solution was washed with sodium hydroxide solution (2M, 2×150 ml), brine (150 ml), dried (MgSO4) and evaporated to afford the title compound as an oil.

Workup

  1. temperaturewas heated
  2. temperatureThe mixture was cooled
  3. extractionextracted with dichloromethane (200 ml)
  4. washThe dichloromethane solution was washed with sodium hydroxide solution (2M, 2×150 ml), brine (150 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-cb3db71340a9438db05cd1d69270c1d5
Source dataset
uspto-grants-1995_12
Patent number
US05478850

Reaction notes

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