Water → Tyrosol

HRID 981976Notes

Reaction equation

HRID 981976 reaction equation
S(C)C.[OH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](OC)=[O:13])=[CH:7][CH:6]=1.C1(O)C=CC=CC=1.O>O1CCCC1>[OH:13][CH2:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([OH:4])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 1068Dimethyl Sulfide2×HCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 10393TyrosolYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of BH3.(CH3)2S (500 mL, 2M in tetrahydrofuran) was added dropwise to a solution of methyl 4-hydroxyphenylacetate (116 g, 0.70 mole) in 300 mL dry tetrahydrofuran. This solution was heated at reflux for 2 hr and stirred at room temperature for 12 hr. TLC indicated the presence of phenol and another 30 mL of BH3.(CH3)2S solution was added. This solution was refluxed for 1 hr, cooled, and then hydrolyzed by dropwise addition of water. The mixture was concentrated in vacuo and the residue triturated with ethyl ether. The ethyl ether portion was dried (MgSO4) and concentrated in vacuo to give 90 g (93%) of 4-(2-hydroxyethyl)phenol, m.p. 84°-86°.

Workup

  1. temperatureThis solution was heated
  2. temperatureat reflux for 2 hr
  3. temperatureThis solution was refluxed for 1 hr
  4. temperaturecooled
  5. concentrationThe mixture was concentrated in vacuo
  6. customthe residue triturated with ethyl ether
  7. dry with materialThe ethyl ether portion was dried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4cca18c090ce4a258fc1af674582ccd6
Source dataset
uspto-grants-1991_02
Patent number
US04994476

Reaction notes

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