Carbon Dioxide → Dimethylphosphono-(2-methoxymethylphenyl)-acetic acid

HRID 36607Notes

Reaction equation

HRID 36607 reaction equation
C([Li])CCC.[CH3:6][O:7][CH2:8][C:9]1[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=1[CH2:11][P:12](=[O:17])([O:15][CH3:16])[O:13][CH3:14].[C:22](=[O:24])=[O:23].C(OCC)C>CCCCCC.O1CCCC1.O>[CH3:14][O:13][P:12]([CH:11]([C:10]1[CH:18]=[CH:19][CH:20]=[CH:21][C:9]=1[CH2:8][O:7][CH3:6])[C:22]([OH:24])=[O:23])([O:15][CH3:16])=[O:17]

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 3283Diethyl EtherHCID 19937177Dimethyl 2-methoxymethylbenzylphosphonateHCID 178418339Butyllithium

Product 1

HCID 19937251Dimethylphosphono-(2-methoxymethylphenyl)-acetic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
20 °C

Procedure

165 ml of a 1.6 M solution of n-butyllithium in hexane was added at (-65)° C. to 170 ml of absolute tetrahydrofuran. At this temperature a solution of 61 g of dimethyl 2-methoxymethylbenzylphosphonate (from Example 8) in 100 ml of tetrahydrofuran was dripped in. After 30 minutes the batch was poured into a (-60)° C. cold saturated solution (500 ml) of dry ice and diethyl ether. After the batch had been stirred for 10 minutes it was allowed to heat up to about 20° C. over a period of 4 hours. 300 ml of water was added and the organic phase was separated off and extracted three times, each time with 100 ml of 100 ml of 10% strength sodium carbonate solution. The combined aqueous phases were extracted twice, each time with 150 ml of diethyl ether, and the pH was adjusted to 1 with 2 N sulfuric acid. Extraction was carried out three times, each time with 150 m]of dichloromethane, the organic phases were dried, and the solvent was removed under reduced pressure. There remained 60 g of dimethylphosphone-(2-methoxymethylphenyl)-acetic acid as a yellow

Workup

  1. additionAfter 30 minutes the batch was poured into a (-60)° C
  2. customthe organic phase was separated off
  3. extractionextracted three times
  4. extractionThe combined aqueous phases were extracted twice
  5. extractionExtraction
  6. dry with materialeach time with 150 m]of dichloromethane, the organic phases were dried
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-acc2a54f37d442768b4ca50eac77a62d
Source dataset
uspto-grants-1995_05
Patent number
US05416068

Reaction notes

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