Sodium borohydride → 4-(3-Chloropropoxy)-3-hydroxy-alpha-methylbenzenemethanol

HRID 2379940Notes

Reaction equation

HRID 2379940 reaction equation
[BH4-].[Na+].[Cl:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][C:9]=1[OH:17]>C(O)C.O1CCCC1>[Cl:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:15])[OH:16])=[CH:10][C:9]=1[OH:17]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 103765071-(4-(3-Chloropropoxy)-3-hydroxyphenyl]ethanone

Product 1

HCID 103989864-(3-Chloropropoxy)-3-hydroxy-alpha-methylbenzenemethanolYield 55%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a flask charged with sodium borohydride (1.5 g, 0.0394 mol) under nitrogen and chilled to 10° was added, slowly, a solution of 1-[4-(3-chloropropoxy)-3-hydroxyphenyl]ethanone (6.0 g, 0.0262 mol) dissolved in ethanol-tetrahydrofuran (120 ml, 2:1). After total addition, the ice bath was removed and the reaction was stirred at ambient temperature for 3 hours. An additional amount of sodium borohydride (0.2 g, 0.0053 mol) was carefully added. After stirring at ambient temperature for one hour, the solvent was removed in vacuo. The resultant solid residue was diluted with water (100 ml) and left overnight. The product was isolated by vacuum filtration yielding 3.8 g. Two consecutive recrystallizations from toluene provided 3.3 g (55%) of 4-(3-chloropropoxy)-3-hydroxy-α-methylbenzene methanol as a light brown solid, m.p.=107°-109° C.

Workup

  1. temperaturechilled to 10°
  2. additionwas added
  3. additionAfter total addition
  4. customthe ice bath was removed
  5. stirringAfter stirring at ambient temperature for one hour
  6. customthe solvent was removed in vacuo
  7. additionThe resultant solid residue was diluted with water (100 ml)
  8. waitleft overnight
  9. customThe product was isolated by vacuum filtration
  10. customyielding 3.8 g
  11. customTwo consecutive recrystallizations from toluene

Sources & evidence

ORD record
ord-51958a8126e34400924bb812f4e3c0d4
Source dataset
uspto-grants-1994_11
Patent number
US05364866

Reaction notes

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