Hydrochloric Acid → 2-(2,6-Dimethoxyphenyl)ethanol

HRID 24707

Reaction equation

HRID 24707 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](CC(O)=O)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl.[CH3:22][CH2:23][O:24]CC>>[CH3:10][O:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[CH2:22][CH2:23][OH:24]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 138316(3,5-Dimethoxyphenyl)acetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 2656332-(2,6-Dimethoxyphenyl)ethanol

Procedure

A solution of (3,5-dimethoxy)phenylacetic acid (3 g) in Et2O (100 mL) was cooled to 0° C. and LiAlH4 (1M in Et2O, 16.8 mL) was added. The mixture was warmed to room temperature and stirred for 5 h, whereupon the pH was adjusted to 5 using HCl (1 M). The mixture was washed with H2O/EtOAc and the organic layer was separated. The aqueous layer was extracted with EtOAc. The combined organic layers were dried (MgSO4) and concentrated in vacuo to give 3,5-dimethoxy-4-(2-hydroxyethyl)benzene (2.8 g) as a crude product.

Workup

  1. washThe mixture was washed with H2O/EtOAc
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae5a074dd2d144a895c715f5decbdd0e
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Linked notes

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