Sodium Hydroxide → HCID 18707489, compound

HRID 1421935Notes

Reaction equation

HRID 1421935 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[CH:5]=1.[OH-].[Na+]>O.C(O)C>[C:15]1([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:24])=[O:2])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54529401HCID 54529401, compound

Product 1

HCID 18707489HCID 18707489, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To the above benzoic acid methyl ester (12.3 g, 40.0 mmol) suspended in a mixture of water (125 ml) and ethanol (125 ml) was added sodium hydroxide (4.80 g, 0.12 mol) and the reaction mixture was heated at 60° C. for 20 h. The volatiles were evaporated in vacuo and to the residue was added water (50 ml) followed by concentrated hydrochloric acid to pH=1. The resulting mixture was stirred at room temperature for 20 h and the precipitate was filtered off and washed with water (3×25 ml), suspended in diethyl ether (100 ml) and stirred for 2 h. The precipitate was filtered off and dried in vacuo at 50° C. which afforded 10.23 g (81%) of 3-(biphenyl-4-yloxymethyl)benzoic acid as a solid.

Workup

  1. customThe volatiles were evaporated in vacuo and to the residue
  2. additionwas added water (50 ml)
  3. filtrationthe precipitate was filtered off
  4. washwashed with water (3×25 ml)
  5. stirringstirred for 2 h
  6. filtrationThe precipitate was filtered off
  7. customdried in vacuo at 50° C. which

Sources & evidence

ORD record
ord-facf62176a59472f8fb8f325b8ca9d32
Source dataset
uspto-grants-2000_06
Patent number
US06080770

Reaction notes

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