Water → HCID 14579128, compound

HRID 330515Notes

Reaction equation

HRID 330515 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:12](O)=[O:13])=[CH:7]2.B.C1COCC1.C([O-])([O-])=O.[K+].[K+].O>C1COCC1>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:12][OH:13])=[CH:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2723981Borane;tetrahydrofuranHCID 146787455-Chloronaphthalene-2-carboxylic acid

Product 1

HCID 14579128HCID 14579128, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred suspension of 5-chloro-2-naphthoic acid (1.10 g, 5.32 mmol) in THF (10 mL) was added BH3.THF (1M in THF, 7.50 mL, 7.50 mmol) over 10 minutes. The resulting mixture was then heated under reflux for 1 hour 30 minutes, recooled to 0° C., and saturated aqueous K2CO3 (4 mL) was added. H2O (20 mL) was added and the mixture was extracted with ether. The combined extracts were washed with brine, dried (MgSO4), and concentrated to give a pale yellow solid (0.94 g, 97%), m.p. 72°-75° C.

Workup

  1. temperatureThe resulting mixture was then heated
  2. temperatureunder reflux for 1 hour 30 minutes
  3. customrecooled to 0° C.
  4. extractionthe mixture was extracted with ether
  5. washThe combined extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-00d8fcdc952c4861ba79afb435b6cfbd
Source dataset
uspto-grants-1990_01
Patent number
US04897405

Reaction notes

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