(1,1'-Biphenyl)-4-methanol → Methyl 4-(4-biphenylylmethoxy)phenylacetate

HRID 1356459Notes

Reaction equation

HRID 1356459 reaction equation
[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.S(Cl)(Cl)=O.O[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:22][CH:21]=1.C[O-].[Na+]>CN(C=O)C.O>[C:1]1([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:2]=[CH:3][C:4]([CH2:7][O:8][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:22][CH:21]=2)=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 19186(1,1'-Biphenyl)-4-methanolHCID 24386Thionyl ChlorideHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 18508368Methyl 4-(4-biphenylylmethoxy)phenylacetateYield 77.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
30 °C

Procedure

A solution of 4-biphenylmethanol (800 g) in DMF (2.4 l) as cooled to 0° C and thionyl chloride (380 ml) was added to the solution for 40 min. The temperature of the reaction mixture was raised to 30±2° C. and stirring was continued for additional one hr. Methyl 4-hydroxyphenylacetate (722 g) was added and stirring was continued for 20 min at this temperature. 28% Sodium methoxide (2.93 kg) was added to the solution for 70 min and stirring was continued for 6 hr while the temperature of the reaction mixture was maintained at 50±2° C. Water (3.21) was added to the reaction mixture for 25 min while the temperature of the reaction mixture was maintained at 50±2° C. which was stirred for additional one hr at same temperature and cooled to room temperature. The precipitate was collected by filtration and washed with methanol (1.6 l) and water (6.41) sequentially to obtain the titled compound (1119 g).

Workup

  1. stirringstirring
  2. waitwas continued for 20 min at this temperature
  3. stirringstirring
  4. waitwas continued for 6 hr while the temperature of the reaction mixture
  5. temperaturewas maintained at 50±2° C
  6. temperaturewas maintained at 50±2° C. which
  7. stirringwas stirred for additional one hr at same temperature
  8. temperaturecooled to room temperature
  9. filtrationThe precipitate was collected by filtration
  10. washwashed with methanol (1.6 l) and water (6.41) sequentially

Sources & evidence

ORD record
ord-b1c150ed45154311ab6003e15d80112f
Source dataset
uspto-grants-2003_07
Patent number
US06586475B1

Reaction notes

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