Hydrochloric Acid → HCID 19744756, compound

HRID 733334Notes

Reaction equation

HRID 733334 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:18]=[CH:19][C:20]=1[O:21]C(C)=C)[C:12]([O:14]C(C)=C)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N12CCN(CC1)CC2.Cl>C(O)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:18]=[CH:19][C:20]=1[OH:21])[C:12]([OH:14])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 9237DabcoHCID 53707616HCID 53707616, compound

Product 1

HCID 19744756HCID 19744756, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of propen-2-yl 3-benzyloxy-4-(propen-2-yloxy)benzoate (1.0356 g, 3.19 mmol), tris(triphenyl-phosphine)rhodium chloride1 (204 mg, 0.22 mmol) and 1,4-diazabicyclo[2.2.2]octane (74 mg, 0.66 mmol) in ethanol (18 cm3) and water (2 cm3) was heated under reflux under an atmosphere of nitrogen for 16 h. The cooled mixture was poured into 1 M hydrochloric acid (100 cm3), stirred for 60 min, then extracted with dichloromethane (3×100 cm3). The combined extracts were dried over MgSO4 and evaporated to an orange solid which was purified by flash column chromatography (eluent: 1:1 EtOAc:light petroleum) to give 3-benzyloxy-4-hydroxybenzoic acid as an orange solid (650 mg, 83%), m.p. 167.2-171.3° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under an atmosphere of nitrogen for 16 h
  3. extractionextracted with dichloromethane (3×100 cm3)
  4. dry with materialThe combined extracts were dried over MgSO4
  5. customevaporated to an orange solid which
  6. customwas purified by flash column chromatography (eluent: 1:1 EtOAc:light petroleum)

Sources & evidence

ORD record
ord-d3afb666ff43401594549acbd07e63dd
Source dataset
uspto-grants-2009_09
Patent number
US07589170B1

Reaction notes

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