3-Hydroxybenzaldehyde → HCID 10035212, compound

HRID 414828Notes

Reaction equation

HRID 414828 reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][CH3:6].II.[OH:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=[O:14].Cl>CCOCC>[OH:9][C:10]1[CH:11]=[C:12]([CH:13]([OH:14])[CH2:3][CH2:4][CH2:5][CH3:6])[CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 5

HCID 1013-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 807IodineHCID 8002Butyl bromide3×HCID 5462224Magnesium

Product 1

HCID 10035212HCID 10035212, compoundYield 221.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
0 °C

Procedure

A dried 1 L 3-neck flask equipped with a N2 inlet, reflux condenser, mechanical stirrer and a 500 ml drppping funnel was charged with 24.3 g (1.0 mol) of magnesium and 50 ml of anhydrous ether. To this was added 15 g (0.11 mol) of 1-bromobutane (Aldrich 23,988-7) and one crystal of iodine. The dropping funnel was charged with 122 g (0.89 mol) of 1-bromobutane and 100 ml. of anhydrous ether. After the contents of the reaction flask began to reflux, the flask was cooled with a water/ice bath and the 1-bromobutane solution was added at such a rate as to maintain a gentle reflux. After the addition was complete the reaction mixture was refluxed for one-half hour, then cooled to 0° C. in an ice/water bath. The dropping funnel was then charged with 38.0 g (0.311 mol) of 3-hydroxybenzaldehyde (Aldrich H 1,980-8) and 250 ml of anhydrous ether. This slurry was added over a 1 hour period. After the addition the reaction mixture was allowed to warm up to room temperature and was stirred overnight. The reaction mixture was neutralized with 900 ml of 5% aqueous HCl. The reaction mixture was extracted with 2×500 ml of ethyl acetate, the organic extracts combined, washed with 1L of water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was recrystallized from ethyl acetate to yield 44.0 g (79%) of 1-(3-hydroxyphenyl)-1-pentanol, m.p. 120°-122° C.

Workup

  1. customA dried 1 L 3-neck flask equipped with a N2 inlet
  2. temperaturereflux condenser, mechanical stirrer
  3. temperatureto reflux
  4. temperaturethe flask was cooled with a water/ice bath
  5. temperatureto maintain a gentle reflux
  6. additionAfter the addition
  7. temperaturewas refluxed for one-half hour
  8. additionThis slurry was added over a 1 hour period
  9. additionAfter the addition the reaction mixture
  10. temperatureto warm up to room temperature
  11. extractionThe reaction mixture was extracted with 2×500 ml of ethyl acetate
  12. washwashed with 1L of water
  13. dry with materialdried over anhydrous sodium sulfate
  14. concentrationconcentrated under reduced pressure
  15. customThe crude product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-57fa8589984d41388ef573066a1af59e
Source dataset
uspto-grants-1988_12
Patent number
US04794188

Reaction notes

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