Citric Acid → 2-[2-(Hydroxymethyl)phenyl]ethanol

HRID 553284

Reaction equation

HRID 553284 reaction equation
B.O1CCCC1.[C:7]([CH2:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](O)=[O:14])(O)=[O:8].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[OH:14][CH2:13][C:12]1[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=1[CH2:10][CH2:7][OH:8]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 66643Homophthalic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 2390242-[2-(Hydroxymethyl)phenyl]ethanolYield 69.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

Borane-tetrahydrofuran complex (1M solution in tetrahydrofuran, 100 mL) was added dropwise over 10 minutes, to a solution of 2-carboxymethyl-benzoic acid (6 g) in dry tetrahydrofuran (100 mL) at 0° C., under nitrogen. The resulting mixture was stirred at 0-5° C. for 20 minutes, then warmed to room temperature for 1 hour. Saturated citric acid solution (150 mL) was added and the reaction concentrated to ˜150 mL. The aqueous phase was extracted with ethyl acetate (3×150 mL). The combined organics were washed sequentially with 1M aqueous sodium hydroxide solution (150 mL), water (150 mL), brine (150 mL), dried (sodium sulfate) and evaporated to give the subtitle compound as yellow oil (3.5 g).

Workup

  1. temperaturewarmed to room temperature for 1 hour
  2. concentrationthe reaction concentrated to ˜150 mL
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×150 mL)
  4. washThe combined organics were washed sequentially with 1M aqueous sodium hydroxide solution (150 mL), water (150 mL), brine (150 mL)
  5. dry with materialdried (sodium sulfate)
  6. customevaporated

Sources & evidence

ORD record
ord-4e919a20e1e44d4d921e55834f2fef0c
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Linked notes

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