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

HRID 2275584Notes

Reaction equation

HRID 2275584 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 it to precipitate the white solid product, which was filtered and dried under vacuum 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 vacuum

Sources & evidence

ORD record
ord-71d047cd08be441fb5c31ded07c466a5
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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