Hydrochloric Acid → 1,3-Benzenediol, 4-(phenylmethyl)-

HRID 1296928Notes

Reaction equation

HRID 1296928 reaction equation
[BH4-].[Na+].C(OC(=O)[O:7][C:8]1[CH:13]=[C:12]([O:14]C(OCC)=O)[CH:11]=[CH:10][C:9]=1[C:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)C.Cl>O.C1COCC1.[OH-].[Na+]>[CH2:20]([C:9]1[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:8]=1[OH:7])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 58913545HCID 58913545, compound

Product 1

HCID 752941,3-Benzenediol, 4-(phenylmethyl)-

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of sodium borohydride (1.85 g, 49 mmol) in water (30 ml) was added to an ice cooled solution of carbonic acid 2-benzoyl-5-ethoxycarbonyloxy-phenyl ester ethyl ester (3.6 g, 10 mmol) in THF (30 ml). The mixture was stirred for ˜60 mins. at 0° C., and for ˜60 hrs. at room temperature, to give a pale red suspension. Water (150 ml) was added and the mixture extracted with diethyl ether (150 ml). The extracts were washed with water (2×100 ml) and saturated aqueous sodium chloride solution (50 ml). The solution was dried over anhydrous magnesium sulphate and concentrated to give a pale yellow gum. The gum was taken up in aqueous sodium hydroxide (20 ml, 10%), and the solution heated under reflux for ˜60 mins. The solution was allowed to cool and acidified with hydochloric acid (5 ml, 37%). The mixture was extracted with diethyl ether (50 ml). The extracts were washed with water (3×40 ml) and saturated aqueous sodium chloride solution (30 ml). The solution was dried over anhydrous magnesium sulphate and concentrated to give 4-benzyl-benzene-1,3-diol as a dark red gum, (2.1 g).

Workup

  1. waitat 0° C., and for ˜60 hrs
  2. customat room temperature, to give a pale red suspension
  3. extractionthe mixture extracted with diethyl ether (150 ml)
  4. washThe extracts were washed with water (2×100 ml) and saturated aqueous sodium chloride solution (50 ml)
  5. dry with materialThe solution was dried over anhydrous magnesium sulphate
  6. concentrationconcentrated
  7. customto give a pale yellow gum
  8. temperaturethe solution heated
  9. temperatureunder reflux for ˜60 mins
  10. temperatureto cool
  11. extractionThe mixture was extracted with diethyl ether (50 ml)
  12. washThe extracts were washed with water (3×40 ml) and saturated aqueous sodium chloride solution (30 ml)
  13. dry with materialThe solution was dried over anhydrous magnesium sulphate
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-1a9028a467e6438dac3ae50e4d5631a5
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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