Potassium Sodium Tartrate → 3-Hydroxybenzenepropanol

HRID 2389343Notes

Reaction equation

HRID 2389343 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10](OCC)=[O:11])[CH:5]=[CH:6][CH:7]=1.CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(Cl)Cl>[OH:11][CH2:10][CH2:9][CH2:8][C:4]1[CH:3]=[C:2]([OH:1])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 15197885Ethyl 3-(3-hydroxyphenyl)propanoate

Product 1

HCID 103518713-HydroxybenzenepropanolYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 3-(3-hydroxyphenyl)propanoate (54.5 g) in DCM (926 mL) was added dropwise 1.0 M DIBAL in DCM (926 mL) at 0° C. over 1 hour under N2 gas atmosphere. 30% Rochelle salt aqueous solution (1.34 L) was added to the reaction mixture with dropping funnel at the same temperature. The resulting mixture was stirred for 7 hours at ambient temperature and the organic layer was separated. The aqueous layer was stand for 2 days and extracted with chloroform(1.5 L) 4 times. The combined organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo to afford 3-(3-hydroxypropyl)phenol (40.2 g) as a yellow oil.

Workup

  1. customthe organic layer was separated
  2. customfor 2 days
  3. extractionextracted with chloroform(1.5 L) 4 times
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-b076e68d1d1e45ebae88c2b5d18b7a82
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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