Methanol → HCID 15662572, compound

HRID 2248187Notes

Reaction equation

HRID 2248187 reaction equation
[CH3:1][C@@H:2]([O:5][C:6]1[CH:17]=[CH:16][C:9]([O:10][CH2:11][C:12]([O:14]C)=[O:13])=[CH:8][CH:7]=1)[CH2:3][CH3:4].CO.[OH-].[Na+].S(=O)(=O)(O)O>O>[CH3:1][C@@H:2]([O:5][C:6]1[CH:17]=[CH:16][C:9]([O:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:8][CH:7]=1)[CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 15662570HCID 15662570, compound

Product 1

HCID 15662572HCID 15662572, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the above ester (2.50 g), methanol (20 ml) and 5 ml of 10% NaOH is stirred at RT for 24 hours. The reaction is then worked up by addition of water and 10% sulfuric acid to adjust the pH to 3 and extraction with ether. The combined organic layers are washed with water and with brine, dried, filtered and the filtrate stripped to give (R)-(-)-4-(1-methylpropoxy)phenoxyacetic acid, [α]D20 -21.369°.

Workup

  1. extractionto 3 and extraction with ether
  2. washThe combined organic layers are washed with water and with brine
  3. customdried
  4. filtrationfiltered

Sources & evidence

ORD record
ord-95fa997269b84bc89e5966917e29cfd8
Source dataset
uspto-grants-1991_08
Patent number
US05037991

Reaction notes

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