Methanol → Sodium 4-hydroxy-4-(2-methylphenyl)butanoate

HRID 322957Notes

Reaction equation

HRID 322957 reaction equation
[OH:1][CH:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[CH2:3][CH2:4][C:5]([O:7]C(C)(C)C)=[O:6].CO.[OH-].[Na+:22]>O1CCCC1>[OH:1][CH:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[CH2:3][CH2:4][C:5]([O-:7])=[O:6].[Na+:22]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 22010446t-Butyl 4-hydroxy-4-(2-methylphenyl)butanoate

Product 1

HCID 23665160Sodium 4-hydroxy-4-(2-methylphenyl)butanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of t-butyl 4-hydroxy-4-(2-methylphenyl)butanoate, thought to be the (R)-enantiomer, (0.5 g) in tetrahydrofuran (3 mL) and methanol (3 mL) is treated with aqueous sodium hydroxide solution (5 N; 0.5 mL) and stirred at ambient temperature for 8 hours. The reaction mixture is concentrated to dryness. The resulting residue is treated with isopropanol (10 mL) and stirred for 30 minutes, and the resulting precipitate is collected and washed with isopropyl ether, to give sodium 4-hydroxy-4-(2-methylphenyl)butanoate, thought to be the (R)-enantiomer, (300 mg) in the form of a white solid, m.p. above 250° C.; 25[α]D=+34° (c=0.01; CH3OH); [NMR(DMSO-d6) (300 MHz):- 1.58-1.75 (m,2H),2.11(m,2H),2.22(s,3H),4.75(m,1H),7.05-7.48 (m.4H).

Workup

  1. concentrationThe reaction mixture is concentrated to dryness
  2. additionThe resulting residue is treated with isopropanol (10 mL)
  3. stirringstirred for 30 minutes
  4. customthe resulting precipitate is collected
  5. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-ced9dd7567274885b3435da95ecb6232
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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