Water → 2-(3,5-Dimethoxyphenyl)ethanol

HRID 1833424Notes

Reaction equation

HRID 1833424 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH2:21][C:22](O)=[O:23])[CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[CH3:20][O:19][C:17]1[CH:16]=[C:15]([CH:14]=[C:13]([O:12][CH3:11])[CH:18]=1)[CH2:21][CH2:22][OH:23]

Participants

6

Reactant 4

HCID 962WaterHCID 24436Sodium SulfateHCID 138316(3,5-Dimethoxyphenyl)acetic acidHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 2656342-(3,5-Dimethoxyphenyl)ethanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-40 °C

Procedure

Within 40 minutes, 1.12 liters of a 20% solution of diisobutylaluminum hydride in toluene is added dropwise to a solution, cooled to -40° C., of 132.3 g. of the methyl ester of 3,5-dimethoxyphenylacetic acid in 1.3 l. of absolute toluene, the temperature rising to -10° C. during this step. After another 20 minutes at -10° C., 151 ml. of water is carefully added dropwise so that the temperature does not exceed +10° C. 200 g. of sodium sulfate is then added to the reaction mixture, and the latter is stirred for 2 hours at room temperature. The solids are filtered off and a subsequent washing step is performed with a total of 1 liter of methylene chloride.

Workup

  1. customrising to -10° C. during this step
  2. waitAfter another 20 minutes at -10° C.
  3. customdoes not exceed +10° C
  4. filtrationThe solids are filtered off
  5. washa subsequent washing step

Sources & evidence

ORD record
ord-79e663ebde5f41d0a8ebf39f8aeb286c
Source dataset
uspto-grants-1978_01
Patent number
US04066674

Reaction notes

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