Carbon Dioxide → 3-Benzyloxy-2-methyl-benzoic acid

HRID 1416078Notes

Reaction equation

HRID 1416078 reaction equation
[C:1](=[O:3])=[O:2].[OH2:4].Cl.[C:6]1(C)[C:7]([CH3:12])=[CH:8][CH:9]=[CH:10][CH:11]=1>C1COCC1>[CH2:12]([O:4][C:6]1[C:7]([CH3:12])=[C:8]([CH:9]=[CH:10][CH:11]=1)[C:1]([OH:3])=[O:2])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:6]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 962WaterHCID 7237O-Xylene

Product 1

HCID 118068023-Benzyloxy-2-methyl-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

232.7 g of 2-benzyloxy-6-chlorotoluene (232.7 g, 1.0 mol) are subjected to a Grignard reaction with 26.7 g (1.1 mol) of magnesium turnings in 550 ml of THF. The brown-black solution of (3-benzyloxy-2-methylphenyl)magnesium chloride in THF formed therefrom is stirred until cold by means of an ice bath at 0° C. CO2 gas is passed into the stirred reaction mixture slowly such that the temperature does not exceed 10° C. The solid suspension in THF formed therefrom is hydrolyzed with cooling by slow addition of 50 ml of water and 445 g (1.2 mol) of hydrochloric acid (10% strength). The hydrolyzed reaction mixture is diluted with 430 g of xylene. The phases are separated and the organic phase is washed with 100 g of water. The product-containing organic phase separated off is distilled until the bottom is free of THF. The bottom is then stirred at 0° C. until cold. The crystallized product is filtered off and washed with 50 ml of xylene. After drying in vacuo, 152.3 g of 3-benzyloxy-2-methylbenzoic acid are obtained. This corresponds to a yield of 62.9% of theory.

Workup

  1. customdoes not exceed 10° C
  2. customThe phases are separated
  3. washthe organic phase is washed with 100 g of water
  4. customThe product-containing organic phase separated off
  5. distillationis distilled until the
  6. stirringThe bottom is then stirred at 0° C. until cold
  7. filtrationThe crystallized product is filtered off
  8. washwashed with 50 ml of xylene
  9. dry with materialAfter drying in vacuo, 152.3 g of 3-benzyloxy-2-methylbenzoic acid
  10. customare obtained

Sources & evidence

ORD record
ord-bd730b561f2f47ac898cb3104219744d
Source dataset
uspto-grants-1999_06
Patent number
US05910605

Reaction notes

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