Hydrochloric Acid → 1-(4-Hydroxyphenyl)cyclopropane-1-carboxylic acid

HRID 969129Notes

Reaction equation

HRID 969129 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:12]([OH:14])=[O:13])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].Cl>O1CCCC1>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2([C:12]([OH:14])=[O:13])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 855751-(4-Methoxyphenyl)cyclopropane-1-carboxylic acidHCID 3611392Lithium tri-s-butylborohydride

Product 1

HCID 225049291-(4-Hydroxyphenyl)cyclopropane-1-carboxylic acidYield 581.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(4-methoxyphenyl)cyclopropanecarboxylic acid (0.70 g, 0.0036 mol) with 1.0 M of L-Selectride® in tetrahydrofuran (18 mL) was microwave irradiated at 120° C. for 2 hours. The completion of the reaction was achieved after LCMS indicated that the starting material was consumed. Then reaction mixture was acidified (pH=2) with concentrated HCl solution. The mixture was concentrated and the residue was diluted with water and stirred at rt to precipitate the white solid product, which was filtered and dried under vaccum to give 3.73 g of the desired product. The structure was confirmed by 1H NMR.

Workup

  1. customwas consumed
  2. customThen reaction mixture
  3. concentrationThe mixture was concentrated
  4. additionthe residue was diluted with water
  5. customto precipitate the white solid product, which
  6. filtrationwas filtered
  7. customdried under vaccum

Sources & evidence

ORD record
ord-8035b35e846d44edad9514d3e4df9892
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

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