m-Phenylenediacetic acid → 2-[3-(2-Hydroxyethyl)phenyl]ethanol

HRID 2382507Notes

Reaction equation

HRID 2382507 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH2:17][C:18](O)=[O:19])[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][C:14](O)=[O:15])[CH:8]=1>C1COCC1>[C:9]1([CH2:13][CH2:14][OH:15])[CH:10]=[CH:11][CH:12]=[C:7]([CH2:17][CH2:18][OH:19])[CH:8]=1

Participants

4

Reactant 2

HCID 29788m-Phenylenediacetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 100807412-[3-(2-Hydroxyethyl)phenyl]ethanolYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a two-liter, 3-necked round-bottomed flask equipped with a 500-ml constant pressure addition funnel, an overhead stirrer, thermocouple and nitrogen inlet was added 16 g (0.42 mol) of lithium aluminum hydride (95%) and 800 ml of anhydrous THF. The addition funnel was charged with a solution of 40 g (0.21 mol) of 1,3-phenylenediacetic acid in 500 ml of anhydrous THF. The diacid was added slowly over a period of 2 hours with cooling in an ice bath. Once addition was complete, the ice bath was removed and the suspension allowed to reach room temperature overnight after which time it was re-cooled and 100 ml of ethyl acetate was slowly added to decompose the remaining hydride. The addition funnel was recharged with 200 ml of 2M NaOH, which was then added slowly with vigorous stirring until the ensuing suspension became granular in appearance. The suspension was filtered and well washed with ethyl acetate. The combined filtrate and washings were then washed with brine, dried over anhydrous magnesium sulfate and evaporated on a rotary evaporator to yield 21 g (62%) of the title compound as a clear, colorless oil.

Workup

  1. customTo a two-liter, 3-necked round-bottomed flask equipped with a 500-ml constant pressure addition funnel, an overhead stirrer
  2. temperaturewith cooling in an ice bath
  3. additionOnce addition
  4. customthe ice bath was removed
  5. temperatureafter which time it was re-cooled
  6. addition100 ml of ethyl acetate was slowly added
  7. additionwas then added slowly
  8. filtrationThe suspension was filtered
  9. washwell washed with ethyl acetate
  10. washThe combined filtrate and washings were then washed with brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customevaporated on a rotary evaporator

Sources & evidence

ORD record
ord-61e94e77ab154bf98bd98354075ec972
Source dataset
uspto-grants-2012_09
Patent number
US08262961B2

Reaction notes

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