p-Phenylenediacetic acid → 1,4-Benzenediethanol

HRID 470969Notes

Reaction equation

HRID 470969 reaction equation
B.CSC.[C:5]1([CH2:15][C:16](O)=[O:17])[CH:10]=[CH:9][C:8]([CH2:11][C:12](O)=[O:13])=[CH:7][CH:6]=1>O1CCCC1>[C:8]1([CH2:11][CH2:12][OH:13])[CH:7]=[CH:6][C:5]([CH2:15][CH2:16][OH:17])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 81760p-Phenylenediacetic acidHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 50132051,4-Benzenediethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-methyl sulfide complex (2M solution in tetrahydrofuran, 80 mL) was added over 20 min to a stirred solution of 2,2′-(1,4-phenylene)diacetic acid (10.20 g) in tetrahydrofuran (100 mL) cooled in an ice bath. After 16 h, the reaction mixture was carefully quenched with methanol (40 mL). The solution was evaporated in vacuo and the resulting gum was partitioned between ethyl acetate and saturated aqueous ammonium chloride. The ethyl acetate solution was separated, dried over magnesium sulphate, filtered and evaporated in vacuo to give the subtitled compound as gum. Yield 8.64 g.

Workup

  1. temperaturecooled in an ice bath
  2. customthe reaction mixture was carefully quenched with methanol (40 mL)
  3. customThe solution was evaporated in vacuo
  4. customthe resulting gum was partitioned between ethyl acetate and saturated aqueous ammonium chloride
  5. customThe ethyl acetate solution was separated
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-fc15ed52d2864bb582b702ff71bed40f
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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